


Cas-a Erotica

by sandean_cas



Category: Supernatural
Genre: Angelic Grace Kink (Supernatural), Angst, Bottom Castiel (Supernatural), Bottom Castiel/Top Dean Winchester, Busty Asian Beauties (Supernatural), Casa Erotica (Supernatural), Castiel Does Not Understand (Supernatural), Castiel Does Not Understand Boundaries (Supernatural), Castiel Does Not Understand Humans (Supernatural), Castiel Watches Dean Winchester Sleep, Castiel Watches Over Dean Winchester, Castiel Watches Porn (Supernatural), Castiel and Dean Winchester Watch Movies, Castiel and Dean Winchester Watch Television, Castiel in the Men of Letters Bunker (Supernatural), Castiel is Not Oblivious (Supernatural), Castiel is Not Okay (Supernatural), Castiel is Protective of Dean Winchester, Castiel is So Done (Supernatural), Castiel's Angelic Grace (Supernatural), Castiel/Dean Winchester First Kiss, Castiel/Dean Winchester Wing Kink, Crack, Dean Winchester Loves Castiel, Dean Winchester Teaches Castiel About Sex, Dean Winchester Teaches Castiel to be Human, Dean Winchester Wears Castiel's Trenchcoat, Dean Winchester Wears Panties, Dean Winchester Worries About Castiel, Dean Winchester is Bad at Feelings, Dean Winchester is an angry sleeper. Like a bear., Dean's Top 13 Zepp Traxx Mixtape, Domestic Fluff, Fake/Pretend Relationship, First Kiss, Fluff, Friends With Benefits, Friends to Lovers, Frottage, Hand Jobs, M/M, Masturbation, Masturbation in Shower, Meta, Metafiction, Misunderstandings, Mutual Masturbation, Not Actually Unrequited Love, Oblivious Dean Winchester, Oblivious Sam Winchester, Other Additional Tags to Be Added, Personal Space, Plot What Plot/Porn Without Plot, Porn with Feelings, Quote: Family Don't End With Blood (Supernatural), Quote: I learned that from the pizza man. (Supernatural), Quote: I'm the one who gripped you tight and raised you from perdition. (Supernatural), Quote: The Meat Man (Supernatural: Atomic Monsters), Quote: Without your power you're basically just a baby in a trenchcoat. (Supernatural), Sam Winchester is Not Amused, Sam Winchester is Scarred For Life, Sam Winchester is So Done, Shower Sex, The Pizza Man (Supernatural), Unrequited Love, Wet Castiel (Supernatural), Wet Dream, Wing Grooming, Wing Kink, Wing Oil, Wingfic, castiel finds dean winchester's porn
Language: English
Status: In-Progress
Published: 2020-01-25
Updated: 2021-01-14
Packaged: 2021-02-27 10:01:42
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 28
Words: 31,855
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22395202
Author URL: https://archiveofourown.org/users/sandean_cas/pseuds/sandean_cas
Summary: “I want you to tell me why my name was on that DVD!” he shrieks.That makes Dean pull up short. Cass is the picture of calm. He doesn’t scream or show emotions in general. “What’re you talking about man?” he asks, forcing his voice not to sound as gruff. He pats the edge of the bed and smiles as the bed dips with Cass’ weight. “Talk to me.”Hands gripping the edge of the bed, Cass gulps, turning his head to Dean. He sees the panic in his friend’s eyes. “I just – I don’t understand things. And what I’m feeling right now… it’s just too much. It feels too intense. And I just can’t breathe. It’s wrong. I know it’s wrong to feel like this but I just – I can’t stop it Dean.”“What can’t you stop?”Eyes, raw and brimming with emotion, Cass stares at him. “Why was my name on that DVD?”“I don’t know.” Dean tries to convey his sincerity. “I really don’t know Cass.”“But it said Cass.” His voice is small. “When I saw it on your bed, I thought it was mine.”A chill goes through him. Cass … he couldn’t mean that DVD… could he?“What DVD?” his voice is almost shrill. It’s like the babysitter and the pizza man all over again.“Cas-a Erotica.” Says Cass.
Relationships: Castiel/Dean Winchester
Comments: 311
Kudos: 900





	1. Cas-a Erotica

**Author's Note:**

> It's me... again...
> 
> So FIFTIETH SUPERNATURAL WORK!!
> 
> I'm so psyched! <3

The bunker is every bachelor’s paradise. Private rooms. Showers. _Locked doors._

And Dean takes advantage of the luxury as much as he can. He lets himself moan a little louder than normal, not having to worry about Sam hearing him from across the room, or through a thin bathroom wall.

He just bought himself the new Casa Erotica Film actually. For a particularly luxurious session that he’s planning for later.

A loud banging noise causes him to fumble with the DVD case.

“Dean!” Sam bellows. “Your bacon grease is in everything!”

Muttering to himself, he tosses the disk aside. “No peace.”

He cracks the door open and glares at Sam. “You little bitch.” He marches away. “Do you see me complaining about the lettuce I keep finding everywhere?”

“Lettuce won’t kill you Dean.” Sam claps back.

“Sure Sammy.” He says. “I’ll put that on your tombstone.”

…

Dean rushes through the dishes and practically bounds back to his room. He locks the door behind him and reaches for his DVD with a huge sigh. ‘Casa Erotica: Loco.’ His dick is literally reaching for it at this point, straining against the zipper of his pants.

He flips the case with a grin. “Ha ha.” Heading over to the DVD player he wonders why it suddenly feels lighter. Only when he cracks the case open does he find out; it’s empty.

Utterly and completely empty.

What the fuck?

His anger and disappointment war with each other. Angry that Sam had obviously screwed with him and disappointment because he really was looking forward to this. After a hatrick of cases that took them from Colorado to Tennessee to Florida and back he needs something to take the edge off before they head out again.

Sure, Dean can just use one of his other movies, or some Busty Asian Beauties, but that just isn’t the same. He pouts, flopping onto his bed.

He’s half-asleep when he hears Cass’ voice. “Dean?”

“Cass.” He mumbles, pressing his face into the pillow. Dean hopes that he’ll just take the hint and skedaddle. But today isn’t his lucky day.

“Dean?” Cass repeats. He waits maybe five seconds: “Dean?”

“What?” he barks.

It’s dark and his eyes are bleary from sleep. All he can make out are Cass’ baby blues and the outline of the trench-coat.

“There seems to be a problem.” Cass states.

“Why don’t you bother Sam?” he huffs.

Castiel seems to consider this, cocking his head and peering down at Dean.

“I thought that I should come to you with this.”

Rolling his eyes, he flops onto his back, fully prepared to hear something about their profound bond.

“You had something with my name on it.” his voice is accusatory.

“No I didn’t.” Dean insists. “Cass… half the time I wonder if you even know how to write. Since when do you write your name on stuff anyway? What are we… in grade school?”

Cass glares at him. “My name was on it.” his voice is dry. “It was printed _very clearly._ It’s a large font Dean. Impossible for even you to miss.”

“Just take it and leave then.” Dean waves him off.

Snuggling down into this bed once more, he tries to latch onto his fatigue and let it drag him into unconsciousness.

“Dean?”

“What?” he demands, throwing the blanket off. “What? What do you want Cass?”

“I want you to tell me why my name was on that DVD!” he shrieks.

That makes Dean pull up short. Cass is the picture of calm. He doesn’t scream or show emotions in general.

“What’re you talking about man?” he asks, forcing his voice not to sound as gruff.

Realising his effort, Cass sighs and bows his head. “Dean, I’m sorry.” He whispers. “I don’t mean to disturb you. This is just so confusing.”

He pats the edge of the bed and smiles as the bed dips with Cass’ weight. “Talk to me.”

Hands gripping the edge of the bed, Cass gulps, turning his head to Dean. He sees the panic in his friend’s eyes. “I just – I don’t understand things. And what I’m feeling right now… it’s just too much. It feels too intense. And I just can’t breathe. And it hurts but it feels so good. It’s wrong. I know it’s wrong to feel like this but I just – I can’t stop it Dean.”

“What can’t you stop?”

Eyes, raw and brimming with emotion, Cass stares at him. “Why was my name on that DVD?”

“I don’t know.” Dean tries to convey his sincerity. “I really don’t know Cass.”

“But it said Cass.” His voice is small. “When I saw it on your bed, I thought it was mine.”

A chill goes through him. Cass … he couldn’t mean _that_ DVD… could he?

“What DVD?” his voice is almost shrill. It’s like the babysitter and the pizza man all over again.

“Cas-a Erotica.” Says Cass.

“Oh my God.” Dean scoots away, pressing a hand to his chest. “Shit you watched that. Shit.” He runs a hand though his hair, no wonder Cass is traumatized. That promised to have some really kinky stuff. “Oh man. I’m such an ass.”

Leaving his porn out. What had he been thinking. He remembers the last time Cass found porn. His eyes drift down. Yup. Little Cass is rising and shining.

And Cass said he felt funny… wrong… dirty. That must be the boner.

“Let me guess.” Dean says, “Your problem is about half a foot and attached to you.”

Contemplating this, Cass waits a beat before nodding.

“Hey!” Dean says brightly. “I have that problem all the time. And let me tell you; it’s mucho annoying.”

“Mucho is a lot in Spanish.”

Dean nods. “Yeah. And Casa Erotica is Spanish too.”

“I know.” Cass says.

“You…” being in such proximity to Cass’ boner makes him a tad uncomfortable, but Dean reminds himself that it would just be a few more minutes. “Watched it right?”

“I did watch some of it.”

“And lemme guess.” Dean looks pointedly downwards. “That’s when your problem popped up.”

A single nod is Dean’s response.

He lays a hand on Cass’ shoulder. “I know. This happens to me all the time.”

“It does?” Cass’ voice sounds almost hopeful.

“Yup.” Dean nods along. He can’t believe that he’s explaining boners to an angel but logic left the chat this is his life ages ago. “But there’s a way to help it.”

Jeez. Can he makes jacking off sound any more like the holy grail?

“Tell me Dean.” Cass squirms slightly, desperation creeping into his voice.

“You saw the guys in the video right?” This is bordering on some – some shit. “That they all had problems too. Did you see what they did?”

“Yes.” Cass sounds uncomfortable again. “But right now, that is impossible for me to do. Unless you and Sam possess multiple reproductive organs.”

Dean cringes. “Nope. Just two red blooded males.” Who knew his porn could provoke such stimulating discussions? Not Dean, that’s for sure. “The stuff they did with their hands.”

“Oh.” Cass’ eyes widen in realisation. “ _Oh!_ ”

Dean chuckles lightly. “Bet that’s the face you make when you finally take care of that.”

He doesn’t know much about Cass’ time with the reaper, but he certainly hopes that he at least got to an orgasm. But then, shouldn’t he know what to do with his dick if he had?

Slapping him one final time on the shoulder, Dean leaves him with a few words of advice. “Just do what feels good.”

…

Dean is having a pretty steamy dream, when he hears his door creak open. He tries to grasp the tendrils of the fast fading dream but to no avail.

Damn it! There were strippers and Jacuzzis and – and Harrison Ford was there.

“Dean?”

The panic in Cass’ voice is enough to wake him completely.

“It isn’t helping. It is not going down. Dean, I don’t know what to do!”


	2. Dean Winchester’s Incomplete Guide To Jacking Off

_“It isn’t helping. It is not going down. Dean, I don’t know what to do!”_

Words Dean never thought he’d hear and words he’d never like to hear again.

“What do you mean it isn’t working?” He demands. “Are you doing it correctly?”

“Yes!” Cass eyes are wide and panicked. “I followed every movement from the screen exactly as it was completed.”

Dean takes a second to blink the sleep from his eyes. When he looks up again, he sees the situation from a new perspective. Cass is too worried to actually _get_ anywhere.

“You’re too tense buddy.” He says. “Try relaxing.”

“Dean. You don’t understand. I can’t relax right now. Not in this condition!”

He feels the on-set of a headache. “You have to relax. I don’t know how else to help you.”

“Dean.” Cass’ voice is desperate. “Please. Help me.”

“I’m trying. I’m trying.” He repeats as he wracks his mind for anything even resembling a fix for this.

“No.” Cass tugs on his sleeve till they’re facing each other. “I mean _help me._ ”

Dean’s eyes flit down, eyeing Cass’ boner in the dim lights. “No way.” He says immediately. “This isn’t my usual area of expertise.”

“You said that you engage in this activity with success.”

He did say that didn’t he?

“But friends don’t do this stuff.” He protests.

Guilt washes over him as he sees Cass’ pinched expression. This is torture for the angel. Stuck with a human affliction that he knows nothing about. If Dean’s dick suddenly stood up and refused to go down without him knowing about sex, he’d be pretty peeved too.

“Okay.” He recants, “Lie down flat on your back.”

He feels disgusting about this. Like his skin is crawling, but this is for Cass. Dean has always believed that sex should be consensual. With someone you find attractive and someone who you can be comfortable with. He half wishes he could buy Cass a hooker and have her go through the motions with him. But that would be cheap – the easy way out – and Cass wouldn’t even like it; if his freak out all those years ago still stands. Dean never saw anyone so frightened by the prospect of receiving a lap dance.

Steeling himself, he clears his throat, as Cass scoots into position. Dean still perches on the end of the bed in indecision. If he’s doing this he doesn’t want to sound uncomfortable and ruin the whole thing for Cass. It’s not that he’s grossed out… Dean just thinks that some lines in a friendship shouldn’t be crossed. And yeah, the idea of being with a guy makes him squeamish.

“Unzip your fly.” He says, keeping his voice even.

His back is turned so he can’t see Cass. But he does hear his zipper loosen.

“Good.” He murmurs. “Close your eyes.”

He feels Cass’ gaze on him and he chuckles. “I can feel you looking at me.”

Cass shifts slightly. “They’re closed.”

Turning slightly, Dean sees that they are, in fact, closed. Cass’ eyelids aren’t the only thing he sees. Standing tall and almost completely flushed is Cass’ dick. He winces, knowing from experience how uncomfortable it can be. He clicks his tongue. It looks a bit chafed too. Dean reaches forward, dipping one hand into his bottom drawer.

Staring at the bottle of lube, he wonders how he’s supposed to get it onto Cass’ dick without crossing any more boundaries.

Eventually, he just settles on, “Stick your hand out.”

He sees the little frown on Cass’ face as the cool liquid coats his palm.

“It’s lube.” He says. “It makes it easier. Just rub it up and down the length and let’s see how that feels.”

Dean grips the edge of the bed to prevent himself from running screaming out of the room as he hears a ‘squelching’ sound. Cass’ breath stutters out and he feels the bed shift.

“Good, huh?” he asks.

“Yes.” Cass all but moans. “What – what happens now.”

“You stay relaxed.” Dean reminds him. “Nice slow strokes from base to tip.”

“Mhh.” Sex noises spill out of Cass lips and Dean can still hear his hand moving.

“Dean.” Dean blows out a breath, shifting as his own pants begin to tighten. It doesn’t mean anything, he reminds himself. When you hear someone – anyone – moan your name so wantonly, you’re bound to pop a boner.

“Try-Try-” Dean stutters, “Twisting wh-when you get to the head. That usually feels pretty good.”

“Ah!” Dean feels the entire bed jerk. “So good.”

“Good.” He parrots… like an idiot.

After a few minutes of staring pointedly at his boner, willing it to go down, he lets out a short gasp, digging the heel of his palm into his crotch to relieve some of the build up.

“You can go faster now.” He says as Cass whimpers on every thrust. “And try squeezing just a bit when you get to the top.”

By now his room sounds like a porno studio. Cass’ moans and pants stretching from wall to wall.

“Dean!” Cass moans. “Dean – Dean something i-is happening.”

“Don’t worry.” He assures. He shifts slightly, getting a better view of Cass’ hand as it flies across his dick, his hips twisting and jerking every so often as the pleasure becomes too much. A drop of pre-cum is leaking and pooling around the crease of the head. The hand that’s not on his dick is fisted in the sheets, cleanching with every gasp and releasing after.

Cass’ eyes are still shut. He’s so close to the big ‘O,’ Dean can tell. Something seems to be holding him back though. Maybe he just needs a little nudge…

“That’s it.” he says using his gentlest voice. “You’re doing great. Just a little more Cass.”

His hand moves even faster and his head tilts back. Dean can even see his dick twitching a bit. “Cass.” He whispers.

“Dean.” He replies.

Cass rips his hand away and punches his bed. “It’s not working!” his eyes crease even as his entire body shudders.

His eyes crack open and he stares at Dean. “Why isn’t it working?”

Dean is stunned. Everything looked fine. The speed, the grip. Dragging his eyes up from his friend’s dick, he focuses on his eyes instead. “Maybe you’re too in your head about it.” Dean says with a shrug.

“No!” he shouts. “I’m trying but nothing is working.” His voice sounds hollow and defeated.

“Close your eyes.” He repeats as he mentally psyches himself up for the vault he’s about to take. He’s about to cross over about a dozen lines.

“Dean, thank you for trying, but this is useless.” Cass sighs, glaring accusingly at his cock. “Maybe, as an angel this isn’t physically possible for me.”

“Close your eyes.” Dean repeats sternly.

Cass glares at him for a few seconds before shutting his eyes petulantly. Dean sucks in a breath and reaches forward slowly.

Warm, is his first thought, as he wraps his fingers around Cass’ cock. He just lets his hand rest for a minute, letting both himself and Cass get accustomed to the feel. When Cass’s face screws up in pleasure and his hips jerk up and twist arcing into his fist, he begins moving slowly.

“Is this better?” he asks. Hopefully, now that Cass doesn’t have to worry about doing the right motions, Dean hopes that he can loosen up enough to finish.

“Dean!” he exclaims, bucking his hips and twisting as thick splashes of come are ejected from his cock. Dean keeps his hand moving slowly, guiding him through the after shocks. Panting slightly, Dean slowly removes his hand and stares at it as it glistens.

Numbly, he rubs his fingers together.

This is Cass’ come. On his hands… on his sheets. On Cass… who is sitting pretty on his bed while staring down at his dick in wonder.

“Dean that was amazing.” He breathes. “Thank you.” Cass’ hands wrap around him, squashing Dean against his chest.

Dean doesn’t have enough mental fortitude to do more than nod and flop onto his bed in shock as Cass walks on shaky legs out of the room.


	3. Come To Me

Dean flops onto his bed, turning over with a groan as his door clicks shut. Something cold and damp has him reeling back. He flicks on his night light. On his sheets – on his bed – the place where he sleeps are globs of Cass’ come.

Words he never thought he would have thunk.

He presses a hand to his forehead. This is going to drive him insane. Why did he do that? It’s not like it’s his sworn oath and responsibility to get Cass off.

It – it’s not like that.

Dean drags his fingers across the hardening globs and sighs.

And to think, this should have been his night, with his Casa Erotica film.

At least someone got to enjoy the night though.

The first time he ever got to see an angel in the throes of passion. Sure, there’d been Anna, but she’s wasn’t all angel at the time. Honestly, he half-believed it when Cass said that angels aren’t made to have pleasure. He never felt so… uncomfortable about being right.

He balls up his linen with a sigh and heads to the bunker’s washing machine.

He moves as quietly as he can with an great big ball of cloth sticking out from his stomach. Lord knows what Sam would do if he were to find Dean actually washing his sheets. He’d suspect something right away and the last thing he needs is for another living soul to find out what he and Cass did in the dark.

Surprisingly, he isn’t alone when he enters the washing area. He senses Cass before he sees him but it’s too late to turn back; the angel is already looking at him.

“Since when do you wash?” Dean asks, not able to maintain eye contact.

“My pants were sticky and cold.”

“Ditto for my sheets.”

Cass looks sheepish. “I never realised pleasure could be so hard to clean.”

“Move it.” he shoos him away from the machine. “It isn’t hard Cass. Look. Just twist and push to full the water and wait.”

As the water begins to fill up, Cass glances speculatively at Dean. “Are things really that simple.”

“Not most things. Just this one.” He pauses. “So um… Cass.”

“Dean.”

“You know… what we did…”

The angel holds up a hand, stopping him. “Dean, there really is no need.” He assures. “I remember what you told me about porn. I assume the same applies here.”

“What did I tell you?” Dean is almost afraid to hear.

“That I’m not supposed to talk about it.” He says, cocking his head. “Have I made the wrong assumption.”

“Nope.” Dean says quickly. “You got it down Cass. Stick to your guns. Don’t talk about it.”

“I’m perplexed though, as to how you were able to complete the process so quickly.”

“Cass, is this your way of not talking about something.”

He glances back at the door. Standing here with Cass and the machine filled with their come stained stuff makes him feel like he’s at the scene of a murder. And not in the calm way he feels when they’re actually _at the scene of a murder._

“I tried so hard.” He says, sounding the slightest bit bitter. “And you were able to do it in no time.”

“Well, now you know what to do.” Dean says, still squeamish. “I guess you just needed a starter course – some training wheels before I let you ride by yourself.”

“Oh, I’m definitely trying this on my own.” He nods to him self enthusiastically.

Dean chances a glance and he finds Cass’ eyes glazed… probably remembering his first orgasm.

“Is it like that every time?” he whispers.

“No.” Dean says, his breath caught in his throat as Cass stares at him. “It gets better.”

It’s just then that Dean notices that Cass is stripped down to his boxers in order to wash his pants. His eyes drift downward and his brain forces him to remember the feel of Cass on his hands. His warm flesh pulsing in his grip, come spurting out from the pink head. Dean’s tongue darts out, moistening his lips.

“While we’re… on that topic.” He says. “Can I have my DVD back.”

Cass looks at him blandly. “But it has my name on it.”

Dean rolls his eyes. “I got it for a reason man. You aren’t the only one with needs.”

“Can’t I just have it a bit longer.” He pleads. “I wanted to try again.”

“Again?” Dean raises his brows. “So soon.”

“I’m an angel Dean, I don’t have to wait.”

Dean doesn’t know what to do with that information. He bobs his head awkwardly. “Sweet. No refractory period. Must be nice. Anyways… I’m heading back to my room.”

…

How is he supposed to exist after that.

The lines had been exploded into a bajillion pieces. Cass hadn’t seemed to realise the significance of what they’d done. He talked to Dean normally when they met in the washing area. He doesn’t understand these things. Boundaries and traditions escape his understanding.

So does that mean Dean should just ignore it.

In friendships things usually go wrong when someone suddenly starts to have feelings. Cass isn’t human. He isn’t privy to human customs. He clearly doesn’t associate sex and feelings. Could it be possible that their friendship could survive his slip up unscathed? 

Still. A larger question remains; why did he do it?

It would have been the easiest thing in the world to just let Cass keep trying or buy him a toy to help out or maybe a tutorial porno. Or any one of a hundred other things that were less intimate than what he had done.

Well, it all stemmed from him wanting to help and to spare Cass the pain and embarrassment of having to go through it alone.

Maybe he shouldn’t compare their friendship to normal ones. There’s nothing normal about it. He’s human and Cass is an angel and they conquer earth shattering problems on weekends. There’s nothing normal that could possibly stem from that. The way they get by isn’t normal. The way they work isn’t normal. Their living situation isn’t normal. The things they do isn’t normal. It stands to reason that sex and friendships shouldn’t be normal either.

A knock on his door distracts him.

“Hey Cass.” He says as his friend pops his head inside. “The sheets are dry?”

“Well… no.”

“You need some help loading them in.”

“No.”

“Throw me a bone here man.”

Cass laughs. “You may find this ironic Dean… did you know that many people refer to erections as boners.”

Oh no.

“So… I’ll ‘throw you a bone.’”

God damn air quotes.


	4. DIY Test Dummy – AKA Dean

“Please tell me you didn’t just say that.”

“I didn’t say ‘that’ I said ‘I’ll throw you a –”

“Stop talking!” Dean presses a hand to his forehead. “Why?” he gestures vaguely downwards.

“I was practicing.” Castiel says with a pout. “Albeit rather unsuccessfully.”

Dread seeps into his bones. He knows why Cass is here.

“What should I do then?” Dean says numbly.

“Maybe you can show me again?” Cass cocks his head innocently.

“No.” Dean says firmly, putting his foot down. “You’re obviously too in your head about this. Dicks aren’t that hard to master. Your technique isn’t bad but you just … think too much.”

“Dean I don’t think my technique is right at all!”

“Just calm down.” Dean almost hides in shame. He’s telling a guy who just discovered the pleasures of having a dick to calm down. “Well… maybe not. But anyway, from what I saw – which was a whole lot more than I wanted to see.” He adds. “Your technique worked just fine. It’s pretty similar to how I do it.” Mostly because he basically dictated it.

He regrets the words as soon as they leave his mouth because of the expression that spreads across Cass’ face. It’s an idea. And Dean can already guess what it is.

“No way Cass.” He takes two steps back.

“But Dean…”

“Cass no.” he’s the one who really understands the significance of having boundaries in a friendship. Cass has no experience, no idea how it could all go wrong. It’s up to Dean to be the adult in this one – to make the hard choices.

“Why?” his friend sounds hurt and Dean feels his will waver.

“B-because.” He says. “Friends don’t do this.”

“But we’re not friends.” Cass says easily.

“Wow.”

Cass sighs in exasperation. “Dean… our bond. You know it can’t be defined as something as simple as friendship.”

Now it’s Dean’s turn to look ashamed. “I know. I just don’t want to screw anything up.”

“You won’t.” Cass assures. “We both want this.”

“Okay.” He sighs in defeat. “So what do you want to do?”

“I want to try my technique out of you.” Says Cass seriously, as though he’s about to start the biggest experiment of his career. Dean half expects him to strap on some gloves and a doctor’s coat.

Well… he feels his blood rush south. That wouldn’t be so bad.

“Lie down.” Orders Cass. “Flat on your back.”

Dean rolls his eyes causing Cass to glare at him.

“I still think your technique is fine.”

Cass shrugs. “Just lie down Dean.”

Flat on his back, staring up blankly at the ceiling, Dean tries to numb himself to what’s happening. His hands are folded over his ribcage, his eyes are shut, he can feel Cass’ gaze on him like a hawk’s.

“Cass?” Dean’s eyes are still shut.

“Why are your eyes closed?” Dean cracks them open in time to see Cass inch forward. “And why are your clothes still on?”

His body trembles at that. His voice sounds sexy without preamble. The innocent way he said the words shouldn’t be causing him to react like this.

“Just unzip the pants.” He whispers.

The atmosphere in the room has changed drastically. They went from playful, friendly teasing, to an intimate moment where Dean feels like he’s intruding on his own self. He’s afraid to raise his voice and break the mood. He’s afraid to move in case Cass takes it the wrong way. He feels like a slab of meat stuck on a spit above an open fire.

“Dean.” Cass says gently. “I know I talked about our bond. That normal doesn’t apply to us. But if you’re uncomfortable, then we don’t have to. I can figure this out some other way.”

Ah. There it is. An out.

But Dean knows he won’t take it. He can already guess the scope of Cass options. Either, he’d suck it up and continue believing that he can’t make it to the finish line or he’d go to some stranger to do what he’s about to do to Dean. Or worse… he’d go to Sam.

“It’s fine.”

“I’m – I’m going to unzip your jeans.” Cass warns.

Even though he knows it’s coming, Dean can’t help the way his hands clench against the sheets or his breath halts at the first contact. The sound of the zip is loud in the room and Cass certainly takes his time undoing it, careful not to hurt Dean.

Dean almost jumps out of his skin as Cass just starts pumping right away.

“Hold it.” he says, trying not to buck them both off the bed. “You gotta start slow.” He cautions. “Try some other erogenous zones and slowly work up to the main event.”

“Erogenous zones.” Cass echoes. “That would be your nipples.”

“Well… yeah.”

Cass smiles at him and he feels some of the tension abate. “I told you Dean, you should have taken off your clothes.”

…

Dean is perfectly naked now, his bare ass touching the sheets. His skin is a sea of tiny goose bumps and Cass, of course, is still fully clothed.

His dick is poking out, slightly hard and rising steadily.

Cass leans over it, peering down in a way that makes Dean grin. His finger gently prods at the joining of the head to the foreskin. “This is an interesting design.”

“Hmm.” Dean says not really concerned about the designs of anything at the moment. “That feels nice.”

Cass looks surprised, but continues the gentle touch some more before trailing his finger down the side and lying on his side next to Dean.

“Nipples?” At Dean’s nod, his fingers reach out to brush the closest one. Cass’ fingertips are rough and unsteady. A beginner’s touch.

“Come on.” Dean jests. “Do it like you mean it.”

Not easily goaded, Cass just shakes his head wryly at him. “I um, actually wanted to try something. From the video.”

“Knock yourself out man.”

Nerves that he never knew existed are suddenly roaring to life. Foreplay is definitely one of Cass’ strong suits. The man has magic fingers.

A wet, warm tongue darts across his flesh, circling just around the nipple. Dean grunts his hand flying up to Cass head to hold him in place. He hasn’t even done anything and Dean is ready to explode.

That must be because he psyched himself up so much earlier. His desire to orgasm had obviously been transferred to this situation.

“Okay.” He tugs gently at Cass’ hair. “Okay. Appetiser’s over. Time for the main course.”

“Why do you keep comparing this to food?”

“Well, sometimes food and sex can go hand in hand.”

“I’ll have to keep that in mind.” Cass says. Dean can see the cogs turning in his mind, trying to figure out the mechanics of food and sex.

“That section is reserved for the advanced class.” He blurts just as Cass’ hand is hovering over his dick.

“Dean.” Cass says gently.

He sighs, “Yeah. I’m good.”

When Cass lubed hand makes its way down his dick, all the muscles in his body spasms. Cass’ hand moves up and down steadily, his thumb flicking past his head every so often, just like Dean had told him earlier.

The pleasure is there for sure, but muted by his internal panic. The fact that this is happening, in his room, on his bed of all places. The fact that Dean was the one who agreed to it, despite his better judgement. If anything goes wrong it’d be all his fault.

He told Cass to lighten up while jacking off and now he can’t even follow his own advice.

Cass’ eyes flit between his hand on Dean’s cock and Dean’s face. With his spare hand, he rubs at Dean’s nipples and traces patterns on his stomach. All the while, blue eyes follow him. It’s a bit disconcerting, he has to admit. Usually, he’d just be able to shut his eyes whenever things were too heated or his emotions were bubbling too close to the surface.

But every time his eyes slip shut, Cass presses the pad of his thumb onto Dean’s eyelids, a silent command to open up.

“C-ass.” He gasps. “This is –” his words falter and disappear from his mouth as Cass picks up the pace.

What was he saying?

“Man, I gotta close my eyes.” He whimpers, his eyes darting left and right to escape the blueness of Cass’ stare. “It’s too intense.”

“Go ahead.”

Dean’s eyes slip shut.

He doesn’t clench his jaw as much. Moans spill past his lips with increased frequency. His hand grips onto Cass free one, using it to anchor himself and now drown in the sensations.

“Cass.” He whispers, losing control of his hips and bucking into his strokes. “Cass.” He repeats. “So close.”

That seems to embolden him. His movements are faster, his grip just a bit firmer. “You look beautiful like this.”

The groan that spills past his lips is sinful and _loud_. It reverberates through the room, shattering any pretences and baring them both.

Dean feels his dick kick as his orgasm roars through him. His ears sound like a river is flowing behind them and his eyes squeeze together even tighter as his hips twist, chasing after his pleasure.

Cass’ hand keeps moving, guiding him through the last pulses.

Dean doesn’t have the energy to do much more than lie boneless on the bed.


	5. Testing A Theory

_“You look beautiful like this.”_

Dean squeezes his eyes together even more tightly. How he can still hear those words past the blood rushing through his ears is unbeknownst to him.

Had he done that? Made those noises. The things he’d done in the heat of passion now shrink back at the first sight of common sense.

And watching Cass play around with his come like a kid with slime doesn’t help his confusion any. His mind is still reeling from the orgasm and Cass sticking his fingers into his mouth is maddening.

He wants to speak. Force some words from his lips to finally end this ordeal. But his tongue is pinned to the roof of his mouth and he struggles to even get a breath out.

It felt good. So effortlessly good.

And it wasn’t supposed to be.

Cass rubs his fingers together. “My methods seemed to have worked on you.” he glances over to Dean, holding his stare. “How was your orgasm?”

Massive. Explosive. Like a bazooka.

“Peachy.” He grunts.

“Dean.” He says drily. “You need to be a bit more descriptive than that.”

“Cass… what’s there to say. It probably felt just like yours.”

He doesn’t want to carry on a conversation after that. He wants to just lie here and mope.

_“You look beautiful like this.”_

Did Cass really say that? Or had he hallucinated it? Dean isn’t sure which one would be worse. His head is swirling and he’s pretty sure his legs are jelly. The fact that he’d come right after those words hadn’t escaped him either. But manual stimulation can get anyone off, right?

“Are you okay?” Cass says gently, seeming to sense his internal break down.

“Yeah.” But his voice comes out rough.

“I don’t understand your reservations about this… but I don’t wish to cause you any discomfort.”

“No.” he breathes out. “Just… orgasms can be tiring. I just need a sec.”

Cass peers down at him. “I don’t feel tired.”

“Course you don’t.” he mutters.

In the typical fashion, he lets two fingers hover over Dean’s forehead. “May I?”

Now that shocks some life back into him. “Wow. You have the magic cure of a limp dick.”

“Of course not.” He seems almost amused. “But… what I _can_ do is heal fatigue.”

“Fix me up doc.” He says leaning into the touch.

A few seconds later and Dean is as spritely as ever. Like he just chugged a gallon of coffee or a Monster.

“This is cool.” He glances down. “I wonder if I can go again.”

Cass winks at him. It’s so out of character and so cringey that he can’t help but laughing.

He looks pointedly downward trying to act natural in the presence of Cass’ erection.

“So, you ready to test your theory?”

Cass stares at him determinedly. “Yes, I am.”

…

Cass glare pouts at him. “I was right.” He says glumly.

Dean sighs.

How could it not have worked. His dick should have been exploding like a bazooka… Dean’s certainly had.

Dean rests his head against the headboard. Staring down at Cass’ pink, erect dick.

“With all those magical angel powers, can’t you just…” he makes a pshew sound and mimics an explosion.

“I can explode monsters easily Dean, you know this.” Cass says in annoyance.

“No.” he can’t believe the flush that dares to creep into his cheeks. “I don’t – I mean can’t you just make yourself orgasm?”

“No.” he murmurs.

Dean scratches his head in indecision. He knows that Cass is still too in his head about this whole thing. Some guys, stimulation is all that does it, but for others and Cass, they need a little something more. Dean has to admit, it does feel nice to build up languidly to a peak though, sometimes he does enjoy a fast and hard orgasm.

The orgasm with Cass had been strange – it fit into neither of those categories. But he’d still gotten to orgasm. Cass hadn’t. He prides himself on very few things; one of which is knowing how to satisfy his sexual partners and giving as much as he takes.

Maybe Cass just needs a confidence boost, he tells himself. Some training wheels before Dean lets him ride solo.

“You’re too in your head.” He reminds. He pauses with his hand hoving over Cass dick. “This is the last time.”

When he brings his fist down, Cass moans at the sensation, his hands wringing at the sheets.

“Dean.” There it is. He always thought that Cass had sex hair… now he knows that he has the voice to go with it. “Ah! Why are you allowed to make me feel this way?”

Dean could ask the same. “I don’t know man.” He says. “But after we finish here, I’m positive that you can do this.”

“Your hands just feel so much better than mine.”

Now that isn’t the attitude he wants to hear. “You’ll come to prefer yours.” He murmurs.

 _“You look beautiful like this.”_ The words come to mind at this moment. There’s something enticing about the way Cass writhes on his bed – under his hand.

“Dean please.”

“Put your hand.” He says in a burst.

Cass hurriedly shifts his hand to cover Dean’s, mimicking the up and down motions. Soon enough, Cass’ hand slows and loses rhythm, actually interrupting Dean’s tandem.

“Cass.” He whispers. “Almost there.”

He receives only as grunt in reply before his hips buck up into Dean’s fist, spilling into his hand.

Dean kind of likes the blissed out, open expression on his friend’s face. He likes that he was the one who put it there.

This time Cass remains in place, sprawled out in his bed, until his body stops trembling.

“I wish I could do that.” He breathes.

“You can.” Dean finds himself saying. “You did it to me after all.”

Cass glances up at that, a slow smile of satisfaction slipping onto his face. “I did, didn’t I?”

Dean shakes his head. Cass is full on beaming now.

“Does this really have to be the last time?”

That breaks the mood somewhat.

“I was hoping that you could help me practice.” Cass presses on.

Dean bites his lip. “About that… your hand… your grip started to slacken way too soon.”

“I couldn’t help it Dean. The pleasure made me lose control.”

“When you… lose your rhythm before the main event, things can go down hill after that.” He explains. “The thing is, you’re not giving yourself enough simulation to get yourself over the edge.”

“So… what you’re saying… is that I need to build up a tolerance… to pleasure.” Cass says slowly. Dean doesn’t even have a chance to reply before he picks up the pace, belting out his next sentence like a round of bullets from an automatic. “Okay. Great. This is perfect. You can help me build up my tolerance. Three times a day should be enough. Or should we start with ten? I don’t know. We can figure this out tomorrow. I can’t believe how great this ‘after glow’ is.”

Cass hops out of his bed.

Dean grumbles as the door slams shut behind him. “That was completely _not_ what I was saying.”


	6. All The Right Moves

Dean locks his room door most of the next day, feigning sleep when Cass knocks.

It’s not that he doesn’t want to help out.

He _does_. And that’s the problem.

Cass is convinced that this changes nothing. And maybe, it _should_ change nothing. Maybe Dean is just too in his head about this. Lord knows he never listens to his own advice.

Cass’ hands had felt so perfect around him. He remembers being so confused as to why they didn’t seem to work on him. It’s a strange thing, experiencing so much sensations that you’re forced to pull back before those feelings release. He understands how that could be both frustrating and confusing. To make himself feel better he just has to remember, that next time, when Cass comes into his room, that Dean makes the entire experience about him. No more letting Cass touch whatever he wants. If Dean is doing this, then it has to be solely about Cass. Not Dean.

Knuckles rap firmly on the door, prompting Dean into action. He cracks the door open, ready to explain his idea to Cass, before he pulls up short in surprise.

“Sam.” He breathes.

“Why are your sheets still in the drier.”

Dean has to fight the flush that creeps up his cheeks. Damn sheets, he completely forgot about those.

“Uh, couldn’t you just chuck them in for me?”

Sam purses his lips. “I already did that. But that wasn’t what I came to talk to you about.”

“What was it then?” he asks, leaning against the door.

“It’s Cass.” Sam says. “You know, he’s been moping around your room for a while. Then he saw me and clammed up when I asked why he was here.”

Dean winces. He remembers making Cass promise that he wouldn’t breathe a word about this to Sam.

“You gonna tell me what’s up with you two?”

“Nothing’s up.” He says, keeping his voice smooth and unbothered. “Maybe he needed somethin’ and I was dead asleep so I couldn’t hear his knocking.”

“You heard mine.” Sam points out.

Why does his brother have to be like this. He rolls his eyes. “I was just starting to wake up Sam.”

“O-kay then.” Sam says, stepping backwards. “Just go talk to him. He looked pretty bummed.”

…

Dean leans back on his heels before knocking at Cass’ door.

Cass pokes his head out, his eyes widening as he sees Dean. “Dean!” he squeaks.

He laughs a bit uneasily. “Sup Cass. Sam says you were lurking.”

Cass shifts slightly. “Well, I remembered out deal. We were supposed to work out the specifics but you were tired.”

“Well. I’m awake now.” He says brightly.

Moaning comes from inside the room. Either Cass is having an orgy or he’s watching porn.

“Is that Casa Erotica?” He pouts slightly. He’s still dying to watch that tape. It’s said to have some of the greatest compilations known to man.

“Yeah.” Cass admits. “Still not much luck.”

“That’s what I’m here for apparently.” He mumbles. He kicks Cass’ room door shut behind them and watches as Cass flicks the video shut. Dean tries not to stare at the lady’s ass as the guy fills her from behind.

“You were getting to the good part, huh?”

Cass nods and gestures for him to sit on his bed.

“I know that you don’t appreciate me putting you in this position.” He begins, “And that you’d rather not do this on the whole. I appreciate the effort you’ve put in so far and I would understand if you didn’t want to continue.”

That hadn’t been what he’d expected.

But, then again, the last few times Cass came to him, he was already drunk on pleasure and that was what his mind was zeroed in on. It makes sense that he’s the one coming to Dean with a rational suggestion now that the hype has worn off.

Dean already knows he won’t be taking the out, but it’s still nice to at least hear he has the option.

“I’m not going to hang you out to dry.” He promises. “What we need to do before we go any further is talk.”

“Okay Dean.”

“So… what do you want from this?” he feels like a damn psych, psycho-analysing every word and intonation for some deeper meaning.

“The ability to feel pleasure like a normal person.”

“Good.” Dean says, clasping his hands together. “Then that’s what we need to focus on. So there are no romantic feelings involved here, obviously. So we have to keep it that way.” Cass nods along. “And when I think that you can have an orgasm without me, we stop. You good with that?”

“Of course.” Cass says evenly. “Dean, what do you want from this?”

“To help you.” he says immediately. What else is there to say?

“And I can help you too.” Cass says causing Dean to frown. “I can practice my hand movements out on you and give you sexual gratification. That way I’m ‘reciprocating.’”

Dean rolls his eyes at the air quotes. “Dude. You don’t need to do that. Like we agreed. This is about you, not me. Let’s keep things simple.”

“If you insist.” Cass says, his shoulders slumping, “But my offer still stands.”

“I’ll keep that in mind.” He promises. No way in hell is Dean going to take him up on it again. It’s a slippery slope after that and Dean doesn’t feel like experiencing the conflicting emotions from last night again.

“Shall we begin then?” Cass asks, eagerness slipping into his voice once again.

Dean rubs his hands together and pushes Cass back onto the bed. “We shall.” He says, purposefully lowering his voice.

Belatedly, he wonders how long it takes to build up a tolerance to pleasure. Because Dean isn’t sure how much longer he can hide the instant erection born from Cass simply removing his pants.


	7. Friends Without Benefits

It’s about five minutes later, when Cass is already half way there, that Dean realises that they never unpaused the video.

“Cass…” Dean lets his voice trail.

Cass pants, glaring down at him as if he just ate the slice of pie that he was saving.

“Do you want me to play the video?” he asks prompting a swift glare from Cass.

“Do you think I care about the video right now?”

“Well, it does have your name on it.” he teases.

“Dean, just… please.”

So Dean doesn’t ask about the video anymore.

At least, not until Cass is finish. His come drying in a puddle on his stomach. Dean runs a single finger over his oversensitive dick one last time before standing and reaching for the tissues. He wipes Cass off and tosses the evidence in the trash.

When he sees Cass preparing to mojo himself back to normal, he lays a hand on his stomach to stop him. “Why don’t you just enjoy the afterglow?”

That seems to be enough, as Cass sinks deeper into the bed, folding his hand’s over Dean’s on his stomach.

“Uh, buddy?” he tugs at his hand slightly to get Cass’ attention. “I wanted to head back to my room.”

“Oh.” Cass almost sounds disappointed.

“And… I’m borrowing Casa Erotica.”

“Oh.” He says again, this time, in realisation.

Dean feels a flush creep up his neck, knowing that Cass will know exactly what he’s going to be doing. Exactly what movements his hands would make as he gets closer to the edge.

“If you want, I could take care of it.”

The ‘no’ that leaves his lips is half-hearted. Cass’ hands had felt nice on him. Foreign. Not like his own, practiced touch and definitely not like the soft, delicate hands of a female.

He reaches to take the disk out from the player, feeling Cass’ eyes on him all the while.

“Minute four.” Cass says as he’s leaving.

“What?”

“Minute four.” Cass repeats. “I think you’ll like that one.”

…

Dean hides the video behind his back at the first sign of Sam. Oddly enough, it was the smell of his shampoo that gave him away, but Dean keeps that to himself as he faces his brother, trying to paste on a ‘natural’ look on his face.

“You talked to Cass, huh?”

“Yeah.” He says, trying to angle against the wall to hide the case from Sam.

“Ok great.” He says brightly. “What did he need?”

“Nothin.” Dean says easily. “Just something about how sleep takes up too much time.” Dean rolls his eyes. “All I ask for is four hours.”

“Right.” Sam says. “And what’s that?”

Dean leans all the way back into the wall, wondering how he can shove Sam off and avoid breaking the disk at the same time.

Unluckily for him, when he tries to evade Sam’s jab at his midsection, his hand jostles the case, and the DVD comes sliding out.

Sam inspects it, amused, “You guys are sharing porn now?”

Keep it cool, Dean, he reminds himself. “You want in Sammy?” he teases, “We split the cost evenly.”

Sam narrows his eyes at Dean, staring at him, trying to discern a lie. Suddenly, his expression brightens.

“Cass.” He says, causing Dean to just about jump out of his skin. “Good to see you.”

“Hello Sam.” Cass says evenly, then turns to Dean. “I thought you were in your room.”

“I thought you were in your room.” He bites out, hoping that Cass can take a hint and leave before Sam starts with his ever so probing questions.

“So, I hear you and Dean are sharing porn now.” He says with forced casualness. “Leme guess, you’re not supposed to talk about it.”

Too late.

He bites his lip, looking over to Cass.

“Dean and I are engaging in something the internet terms, ‘mutual masturbation.’”

Well, Dean waves the last shreds of his dignity goodbye.

“Though, it’s not very mutual at the moment as Dean has stolen the porn.”

To his surprise though, Sam just laughs. “Dude. Be real. If you want to know something about porn or sex you’re better off asking me.” he turns to Dean then. “You probably traumatised him with that! What were you thinking?”

But Sam seems more amused than anything. He clearly doesn’t believe what Cass had said. He thinks that Cass is making some sort of joke. Dean sighs in relief, forcing out a laugh.

“It wasn’t that bad was it Cass?” he asks.

“I did lie prone on the bed for minutes after the video was shut off.” Cass says, throwing a cheeky glance Dean’s way.

Dean doesn’t share his frivolity in dealing with this issue.

Sam just laughs again though, oblivious to their silent conversation. “Dean, you really had me thinking that you two were in some kind of secret relationship or something.”

“A secret relationship?” Cass cocks his head.

Oh no.

“Well, maybe more like a friends with benefits situation.” Sam decides.

Cass says nothing, but Dean can see the gears turning. He has half a mind to turn off the internet in the bunker to prevent Cass from googling ‘friends with benefits.’ Poor guy would be _really_ traumatised then.

Especially if he found the weird shit about them online.

It’s not that Dean had wanted to look. It was more like he _had_ to look. After Sam had teased him on and off for days, Dean had taken to the internet to find out _why_ everyone thought that he and Cass would be a couple.

He’d been bombarded by articles, depicting every detail of their ‘love story.’ From how his first love was Cassie so his last must be Cass to the in depth analyses of their ‘meaningful stares.’

The fan art had been nauseating.

The written pieces, skin crawling.

Dean could barely recover from seeing it. He can’t imagine what Cass will go through.

…

“Dude!” Dean slams the door shut. “What were you thinking?” he demands, tugging at the collar of Cass’ trench coat.

The angel merely glances at him with a neutral expression. “Sam would have never believed what I just said.”

“You don’t know that.” Dean argues.

“Yes I do.” Cass reiterates, but his tone is off this time.

Interesting.

Dean will have to do some digging.

But not before he _finally_ gets Cass out of his room, and tunes in to this ‘minute four’ in the video.


	8. Minute Four

It takes a gargantuan effort to convince Cass to well… ‘get out of his ass.’ In the metaphorical sense of course. Cass has never been and will never be in his ass physically.

When he’s finally alone, he locks the door considers painting some angel warding. Ultimately he decides he just _can’t_ wait any longer to get it on.

Dimming the lights, Dean settles into the darkness for a moment before flicking on the TV and stuffing a hand into his pants, lightly stroking himself within the confines of his jeans.

Dean considers just fast-forwarding to minute four, but then decides that it’s better if he just waits and lets the anticipation rise. He’s been wanting to do this for some time so he doesn’t expect it to last too long. But… he’s been wanting to do this for some time, so he doesn’t want the show to be over too quickly either.

So, Dean figures four minutes is enough to bring himself to the brink. Then when whatever Cass thinks is so sexy comes on, he’ll let that finish him off.

The video starts out classic. Some spanking and girl on girl action that might have been taken straight from his fantasies. What he likes most about Casa Erotica, is the story. With the spanking, it’d been a chick who’d gotten caught trying to steal some make-up from a store. With the girls it’d been some racy step-sibling thing that hadn’t really made much sense.

Well, win some lose some.

It’s the supercut anyway, there’s bound to be tons of sexy stuff even after Cass’ wondrous fourth minute. And that’s not even talking about the other options in the start menu.

He doesn’t understand how they managed to cram so much information into one little CD. Doesn’t matter though, cause it’s a steal of a deal as far as porn is concerned.

Dean’s thoughts become scattered as he sees the timer nearing the third minute, the sheer anticipation of what’s to come has him on edge already. He times his strokes, alternating between fast and slow to make sure that he can last till the good stuff.

When the timer hits 3:59, Dean’s hands pick up the pace again. The scene with the loud screaming orgasm suddenly cuts. He sees the camera shuffling around as it settles on two guys lying together in bed.

“Dude I’m hella horny.” The first one says, running a hand through his blonde hair.

“Same here.” Says the other one, pushing himself onto his feet. “Mind if I use your bathroom?”

The first guy screws up his face. “Gross.”

Dean slows his strokes.

Hmm.

What’s in there? A hot chick? Or is she going to come in while the other guy is in the bathroom. The film’s about due for a threesome, now that he thinks about it.

Dean holds himself in a lose grip, letting his thumb glide back and forth over the head of his cock. Keeping his legs still is becoming more and more challenging and he waits to see what happens.

He glances at the timer to find that they’re only ten seconds in to minute four.

“Wait.” The first guy says, moving onto all fours. “We’re both horny. Let’s do something about it.”

Dean feels his hand still in shock.

Gay porn?

“Damn it Cass!” he mutters, shaking his head.

Next time he has to veto what crap the angel’s watching. What if he sees this and decides that this is what he’s doing with Dean? What if he decides that this is something normal?

He’s already told Sam all their secrets. You can only hear ‘your brother and I are wanking off together’ so many times before common sense kicks in.

Dean doesn’t want to wait for Sam’s common sense to kick in before setting things straight with Cass.

It would be a shame to let all his effort go to waste though. Dean pauses the video and shuts his eyes. He kind of remembers some of his ‘cartoon porn’ as Sam likes to call it.

With those images in mind, his hand flies across his dick , searching for a quick release.

He remembers this little blue haired character. Boobs for days and eyes like sunshine.

Dean presses his eyes together tightly. So blue…

_“You look beautiful like this.”_

His eyes snap open, darting to the door immediately; to tell Cass to stop interrupting him. But no one is there.

Once more, he lets his eyes slip shut, his hand moving in full strokes across his dick. He bites down on his lip as he feels himself get closer. His hips move of their own accord and the muscles in his legs tremble with pleasure. His balls pull up, in preparation to spill his load.

His mind chooses that moment to conjure up the image of Cass lying in this exact position on his bed. His legs flailing and Dean’s hand wrapped around him, stroking him to completion. The sounds that came from his lips are exactly like the noises that Dean is holding back now. The peaceful, blissed out expression on his face is what drives Dean over the edge.

His hand works furiously and his hips stutter upwards ever so often, chasing after the sensation. He feels the cold splatterings of come hitting his chest and stomach. Dean’s breath comes out in harsh pants as the aftershocks flow through him. His hands rests limply on his dick and his body feels sticky with sweat.

Minute four.

What a hoot.

Now, he needs to work on convincing Cass that this thing between them isn’t normal. Because, somehow, Cass had managed to convince _Dean_ that this is normal.

“Damn it Cass!” he mutters again, using his pants to wipe the drying come off of him.

Dean tries to close his eyes and enjoy the afterglow… but all he can see is blue.


	9. Casa Erotica v.s. Busty Asian Beauties

When Dean finally collects himself, he manages to move all the way over to the door before diving right back into bed.

Where is he going? There’s still jizz on his hand. Ugh. He wipes of off on the sheet. And slaps himself upside the head.

“Time for another bath.” He grumbles.

Yanking out the sheets from his freshly made bed, Dean once again curses his carelessness.

He’s the most careless person he knows, other than Cass of course, who had let it slip that they were engaging in mutual masturbation.

Hmm.

Dean remembers his ‘deer in the headlight’ look afterwards, when Dean had confronted him about the whole not telling Sam rule.

He needs to do some digging. Could Sam have found him that first night? He’d found Dean’s sheets rather easily, and finding an angel who doesn’t sweat, pee or poop laundering his sheets and underpants must have run a few alarm bells for his baby brother.

“We meet again.” Sam’s voice says, almost causing Dean to drop his sheets.

“Sam.” Cass says shortly.

Oh, it’s about to get juicy, Dean can tell. He balances the sheets on his side, and leans closer to the open doorway to get a better look.

“Washing again I see.” Sam says. Dean can hear the suspicion in his voice.

“Well, after the ‘mutual masturbation’ my sheets were in need of a rinse.”

Dean feels his heart constrict.

Damn it, Cass!

What does he think he’s doing? Sam is already so suspicious. This is just making it worse.

“Yeah.” Dean sighs. Thankfully the disbelief is even more evident. “Right.”

Cass remains silent and Dean hears the washing machine turn on.

He gathers his sheets and hightails it back to his room.

…

Dean has officially given up on figuring out why Cass and Sam were talking about _that_. Instead, he chooses to spend his time in a more productive manner – in bed, with his hand down his pants.

There’s no Casa Erotica this time, Dean’s gone back to basics: Busty Asian Beauties. Tried and true and hasn’t failed him yet.

Of course Cass chooses that moment to come knocking at his door. He knows it’s Cass because of the timidity of the knock. Sam would just bang down his door without consideration.

“Come in.” he calls.

Maybe he should take to hanging a sock on his door.

As Cass makes his way into the room, Dean wonders whether he should ask him about his and Sam’s little tete-a-tete.

Nah, he decides, he’ll save that for if he catches them again. Curiosity does gnaw at him. Why would Cass break his promise? Does he really think that Sam will just keep on believing that Cass is kidding if he keeps saying it?

“Hello Dean.” Cass says, immediately heading for his bed.

“Is it that time already?” he jokes.

Cass’ expression pinches. “No. I actually just came here to talk to you about…” As his voice drifts, so do his eyes. They land on the magazines in Dean’s lap. “Busty Asian Beauties.” He murmurs.

“The bustiest.” Dean replies.

“What did you want to talk about?”

“Porn.” Cass says immediately, his eyes darting to Dean’s.

“Well… good timing then.” He keeps his expression pleasant, though internally he shudders. Minute fours still haunts him.

“Which do you prefer?” Cass asks, his expression guarded.

Dean gets the feeling that this is about something more than porn. But what answer does Cass want. He just decides to go with the honest answer for a change rather than psychoanalysing the situation.

“Busty Asian.” He replies.

By the way Cass’ expression closes off, he’d say that’s the completely wrong answer. Ugh. Should have gone with the psychoanalysing manic approach.

“Thank you Dean.” He says stiffly. “I’ll head out now.”

Dean frowns. “Hey, don’t. What did you really come in here to talk about?”

Cass stares at him for a long moment. “Minute four.” He says dejectedly.

Ah. Cass had recommended minute four, in the hopes that Dean would like it as much as he did.

“It was… certainly surprising man.”

“You didn’t like it.”

“No.” Dean blurts. “I was just… shocked. I thought that it was just… look it doesn’t matter. Not everyone has the same taste. It’s perfectly normal for guys to like different stuff, even guys who are best friends. So don’t let me discourage you. Stick to your guns.”

Surprisingly, that does little to soothe Cass distress.

His eyes flit over to the magazine once more then back to the door.

“Dude.” Dean says, pushing the magazine off the bed. “What’s up with you today?”

Cass fidgets, rubbing his hands together. “I’ve been lying to you.”

Not shocking, but he hadn’t expected Cass to admit it right away either.

“The reason I told Sam about us earlier was because…” he looks down, embarrassed. “I wanted him to think that we were together.”

Dean frowns. “Why?” He’s pretty much gotten over the anger about that incident.

“Because I wanted to know what it feels like.” Cass whispers. “To have someone think that you’re in a relationship. I’m so sorry Dean. I understand that you’re angry that I broke your trust and betrayed you. I – I’m just sorry.”

A dozen things all connect in Dean’s head. “You have a crush on Sam?” His voice is shrill. He doesn’t know how he’s supposed to feel about this. His brother and his best friend…

“No.” Cass says instantly, cutting his machinations short. “Please stop. I don’t have a crush on Sam. Or anyone really. I just wanted to know what real intimacy feels like. I thought I could mimic it by myself, with my own two hands, but that did not work. Then with you, I felt something… something that I imagined intimacy would feel like. I guess I just wanted to hold onto that… to flaunt it.”

Dean feels his heart constrict. “I understand.” He murmurs, he’d felt this feeling before. The yearning for something more with someone who could understand. “This is normal Cass so don’t feel that it isn’t. I feel this way sometimes and I’m sure Sam does too. Most people have the chance to do something about it when they feel this. But we’re not normal and me and Sam, we usually just plough past it because that’s what we were taught to do. It’s not fair to expect the same from you.”

Cass blinks at him. “You’re not mad?”

“Well, I kinda was. But I’m okay now.”

He gets a small smile and a head tilt. “Good.” Cass says. “I’m still sorry I used you like that. I won’t let it happen again… after all, you were just trying to be a good friend.”

Dean feels his head spin with insanity as Cass stands again.

“Wait!” he blurts.

Halting, Cass turns to face him with a curious expression.

“I know you Cass.” Dean says firmly. “You’re not getting out there anytime soon. You deserve to feel all the things you want to feel. You and me Cass.” He offers, holding his hand out. “I can show you what it means to be close.”


	10. Close

Since that day it’s been a constant barrage of _Cass_. Day and night thanks to that super-charged libido of his. Dean can barely keep up. But he has to admit, it’s some of the best sex he’s ever had. It’s just something about them being together. Him and Cass. He can be free with him. There’s no worrying about condoms and trying to find some leverage in the back seat of the Impala. No worrying about Cass turning out to be a demon sent to seduce and kill him.

The sex is _fine._

Not that they’ve had sex yet. Dean still isn’t comfortable moving past an under the clothes hand-job and wanking off next to each other. When that happens, he still has to reach over and take care of Cass’ problem… since they’re still not sure what’s causing that.

It’s only been a few days. He’s working up to the more raunchy stuff anyway. He’s kind of hoping to get out of this before the actual sex part comes up. He isn’t sure how he feels about that. Giving or receiving.

Sam, of course, remains utterly oblivious, and now that Cass isn’t intent on telling him all their secrets, he’s bound to remain that way unless he walks in on them.

Which he won’t.

Dean is like a hawk when it comes to keeping the door locked. No way is he risking Sam seeing them like that. Honestly, Cass doesn’t seem to mind one way or the other, but he does try to keep it a secret for Dean’s sake. After all, this is a favour.

“Dean.” Cass says.

Dean hums a response, still drained from their most recent rump.

“Can we try something more intimate?”

Dean raises his brow. “I’d say we were pretty intimate, man. What are you thinking about? Graduating to the High School of Blow-Jobs?”

Cass flushes at that. “This is sexual intimacy.” Cass says, ignoring his blow job, jab.

“So, you don’t fancy blowjobs.” That’s a relief. Sort of.

Ever since they began working on being ‘close,’ Cass convinced him to ditch the ‘only for Cass approach.’

‘If Cass comes, Dean comes with him.’ Which, he actually said. In the middle of a sip.

He wasn’t happy about being drenched in fluid. Well, _that_ particular fluid anyway.

So that means if he blows Cass, then Cass will want to do the same. Dean doesn’t know how he feels about that.

“Of course I’m interested in blowjobs.” Cass says evenly. “I just don’t want to rush you.”

“I’m down.” Dean says shakily.

Cass nudges him with his nose. “No. You’re not.” Instead of pouting, he grins predatorily at Dean. “That’s fine. I can wait. I have you all to myself.”

He chuckles at that even as it sends a tingle down his belly. “That’s… very possessive of you Cass.”

His friend just shrugs and continues looking at him.

“I’m talking about a different type of intimacy.”

“Like?”

“Kissing.” He says is quickly then looks away.

That’s good, cause Dean isn’t sure what his expression looks like now. Kissing is for couples. Not for a ‘best friend helping out another best friend’ situation.

“Sure.” He says. He’s blown all the other rules to hell anyway. It was only a matter of time before this one came crashing down too.

Cass blinks, clearly surprised.

“Come on.” He encourages, leaning closer and sticking out his tongue. “I’ll teach you how to French.”

“I’ve – I’ve read about that.” Cass stutters.

Dean grins. “Reading? Let me tell you, doing, tops it all.”

Licking at his lips, he moves closer, keeping his eyes open a crack to monitor Cass’ expressions.

He starts off slow, not wanting to make him feel overwhelmed. Dean licks around his lips, pressing them together lightly before introducing his tongue. Cass uses his own tongue after a few seconds, quickly catching onto the rhythm. Somewhere along the road, Dean lets his eyes slip shut. Cass is obviously enjoying this.

 _Dean_ is enjoying this too, if he lets himself be honest.

It’s been a while since he’s had someone he could just kiss for the hell of it. He has to agree with Cass; kissing is a different kind of closer than sex. Dean thought he already knew that… but kissing’s never felt like this.

He’s relaxed. Cass is giving as much as he takes. He’s in his bed; which is always a plus.

When Cass backs away, Dean finds himself short of breath. Panting, he flops back onto his side of the bed, staring at Cass out of the corner of his eyes.

He too wears a dazed expression. His head, lolling to one side. Though he’s not short of breath, his lips are pink from rubbing against his. Or maybe it’s his scruff. Either way, Dean is all kinds of turned on.

…

“Sam.” He says in greeting, as he ambles into the kitchen.

Who knew kissing could be so dehydrating. Well, it stands to reason, they’ve both been swapping spit for the past couple hours.

Dean’s head still feels fuzzy and heady.

“Woah.” Sam says. Standing immediately.

He’s looking at him like he has **‘I SMOOCHED CASS’** in big bold letters on his head.

“You look … happy.”

Dean stops short. “And that’s a bad thing?”

“No.” Sam says instantly. “Of course it’s not. You deserve to be happy. It’s just…”

“Why.” Dean says knowingly. “You want to know why I’m happy.”

“Yeah.”

“When you find out, let me know.”

Sam scoffs, ducking his head.

“It’s strange, you know.” He finds himself babbling. “This is … the greatest I’ve felt in a while.”

“You look it.” Sam affirms.

A beat of silence passes between them as Dean gulps down his water.

“So um…” Sam says slowly, locking eyes with Dean. “Could it be Cass?”

He almost chokes.

“I’m sorry?” He demands shrilly. Had he revealed too much?

Sam rolls his eyes. “You two have been getting along so well lately. It’s nice to see. Maybe reconnecting with him is what’s making you happy.”

That gives him pause. Maybe it’s not the kissing and the sex stuff that has him feeling this way. Maybe it’s just like Sam says: just _being_ with Cass, in any capacity, is improving his mood. They’re normally either at odds with each other or working a case. The downtime in between is hardly enough to do much more than rest before the next big event bowls them over.

Cass is open with him, tells him his wants and desires and Dean and Cass listen to each other.

It’s like Cass said: they’re getting close.


	11. An In-depth Analysis Into The Rules of Dating

“That… makes sense.” Dean admits reluctantly, he doesn’t want to give Sam the satisfaction of being right, but he doesn’t want Sam to _actually_ be right.

“I do have a question though.” Sam says, seeming genuinely curious.

Dean feels a little more secure in himself now that he knows he isn’t falling for Cass. That would be absurd… and very bad form for a wing man.

“Why is Cass always in your room? What do you guys do?”

“We – we –” Dean scrambles for something. “Hang out.”

Sam stares at him expectantly. “For hours?”

“Well… I’m teaching Cass how to sleep.” … ~~with another person.~~

Sam blinks at him in disbelief. But as the seconds elapse, his expression becomes excited. “Why is the washer always full? Why is Cass washing his clothes all of a sudden?”

“Yes.” Dean says. “He’s… looking for the full human experience.” ~~of being in a relationship.~~

Gullible as ever – thank God for that – Sam eats up his half-assed explanation and begins gushing. “Maybe I can teach him some stuff. I bet that was what you had the porn for too. This has so much potential Dean. I can teach him about healthy livi-”

“Woah!” Dean shouts. “You aren’t allowed to pollute Cass with that nonsense.”

“Who says?” Sam claps back. “If Cass says he wants to learn, then you can’t stop me.”

Oh yes he can. No way is he letting himself be outnumbered.

Belatedly, he wonders how Sam would react to their current arrangement.

He suspects some surprise, indignation maybe. Sam would probably accuse him of some trickery, which, yeah, on any other occasion. But what if Sam is already suspicious? He certainly seems to be looking at him strangely today. Sam is good at piecing things together. What if he thinks that he’s figured it out and is just goading Dean? What if he thinks that Dean and Cass are having sex? Or worse… that they’re actually in a relationship? His implications have become less implicating and more like thinly veiled accusations.

‘Why is Cass always in your room? What do you guys do?’

‘Why is the washer always full?’

‘Why is Cass washing his clothes all of a sudden?”

He seemed to buy the ‘human experience’ thing, but Dean doesn’t want to take any chances. If Sam finds out, he’d be incorrigible.

Dean needs a way to make things seem as platonic as possible. The idea he has is unorthodox in the strangest of ways.

It breaks all the rules of dating – namely the most important one: never bring a third wheel on a date. But Dean’s been breaking all the rules he knows of in recent times; what’s a couple more? Especially if it means that he can get Sam off his back.

Besides… it’s not like they’re _actually_ dating.

Actually, he considered asking Cass to go on a date, so that he could experience that part of intimacy. But the thought seemed ludicrous for numerous reasons. Cass doesn’t eat. He’d just be doing it to placate Dean, which defeats the whole exercise. Being around people doesn’t interest him. Cass isn’t a sports fan, nor does Dean think he can swim which hacks off a good portion of his usual ideas for dates. Plus, the purpose of a date is to have a connection. They already have that.

Maybe they just need to tap into it.

That would still mean finding a way to go out without Sam thinking they’re up to something. After all the ‘jokes’ from the past few days, he’s probably already suspicious.

But what if Dean could make it seem innocent. That way Sam isn’t suspicious, and he still gets a chance to hang out with Cass.

It’s like Dean always says…

If you can’t beat them, make them join you.

By including Sam, he not only squeezes in some precious brother bonding, but he also can take Cass out on an unofficial date.

There’s no way he can actually _take_ Cass out on a date without Sam noticing. And no way is he resorting to sneaking out of the bunker like a couple of teenagers. Especially since the obnoxiously loud bunker door would give them away immediately. Not to mention that Sam’s favourite spot to read is near the stairs.

Or, on some occasions, _on_ the stairs.

What kind of maniac even does that?

After a late night out, Dean remembers walking down the stairs, drunk off his ass. In the darkness he almost broke his neck while tripping over his sleeping brother. They literally have hundreds of chairs for Sam to sit on. And if chairs aren’t his fancy, there’s always counters, and table-tops and… the floor.

But that isn’t the point.

Taking Cass out for a real date would get them caught. That’s where his plan comes in.

Maybe this ‘closeness’ can bring them all together. Kind of like a team-building exercise. Where two thirds of the team are secretly boning. Not just boning, he reminds himself. He’s like Cass’ emotional support dog, who also specialises in sex stuff.

Wow, that sounds weird.

“In the spirit of closeness.” He says, watching Sam for his reaction. “Why don’t the three of us go out for dinner?”

“The three of us?” Sam clarifies.

“Yes, is there someone we’re forgetting?” he asks sarcastically.

“No. No.” Sam assures, still looking at him curiously. Like he’s one of those weird crosswords Sam likes to solve. “It’s just, I thought you and Cass should go to dinner alone. Capitalise on your time together. It’s already making you this happy.”

“What good would that do?” he spends so much time with Cass between the sheets now that he’s barely communicated with Sam in any sort of meaningful way. But now that he’s started ‘communicating again’ he can’t help but start babbling. “If Cass and I go out together, then it would be like a date. But if you’re there, it’s more like a group meeting!”

Sam looks bewildered. “What about when you and I go out?” Sam wonders.

Good point. “Well… we’re brothers.”

“Cass is family.” Sam argues.

“But people don’t know that.” Dean stresses. Why can’t Sam just blindly accept something for once in his life?

“People don’t know that we’re brothers.” Sam says, logical as ever.

“Damn it Sam!” he hisses, feeling flustered. “I just want all of us to hang out and you need to nit-pick every damn detail.”

“Technically, you’re the one nit-picking Dean. You’re inviting another person so it won’t seem like a date.”

“That isn’t nit-picking!”

“Yeah.” Sam seems amused now.

“But you’ll be there? Right?” Dean asks.

Sam rolls his eyes. “I don’t understand this sudden need for team-building, but sure.”

“Great. Our meeting is at eight tonight near the map table. Wear something fancy.”


	12. The Ultimate Third Wheel: Starring Sam Winchester

This morning Sam thought he was acting weird, but they both chalked that up to Dean and Cass getting back into groove. Little did Sam know that getting back into groove involved a whole lot of grinding and a tonne more kissing. And also an undercover date that promises to be one of the most awkward things Dean will ever experience.

Dean hopes that Cass won’t need much convincing.

He raps on Cass’ bedroom door, wondering why he even bothers anymore. It’s not like there’s anything left to see. Dean’s pretty sure he has the size, shape, colour, grit and texture of the goods engraved in his mind.

“Dean.” Cass’ voice comes before he even opens the door.

“Heya Cass.” He replies.

“Are you ready again?” Cass wonders. “I’ve been meaning to talk to you ab-”

“Can we… put a pin in that?” he wonders.

Cass seems perplexed but nods. “Sure.”

“So I talked to Sam in the kitchen.” Dean says. “I think he’s suspicious.”

Cass doesn’t take that information well. He waves his hands wildly and practically drags Dean into his room, shutting the door silently behind him. “Dean, I can’t believe that this happened!” Cass panics. “Did – did he hear something… or see? No I would have sensed him if he were close enough to see.”

Dean quells the urge to point out that while in a state of passion, Cass won’t know if an elephant is close. It’s just how he is. He gets into the act so completely.

“Relax.” Dean cuts his tirade off. “I have a plan to fix things. He doesn’t know anything concrete but we can throw him off.”

Cass seems to have calmed, knowing that Dean has a plan. “What are we going to do?”

“We’re going to…” Dean bites his lip in anticipation. Cass is going to _love_ his plan. They always work well together on cases – the case where they got to dress-up as cowboys pops being a prime example. It reasons that they’ll have just as much fun working together on something that’s not a case. Now that he knows their power, he can’t help but think of all the pranks he can pull on Sam. But Cass is staring at him expectantly, and his dramatic pause is becoming less dramatic and more annoying.

“Dinner.” He finishes with a flourish.

Unfortunately, Cass doesn’t share his giddy enthusiasm. He just seems even more confused.

“You don’t like it?” Dean pouts, his shoulders slumping.

“No.” Cass says quickly. “It’s not that I don’t like it…” Dean waits expectantly. “Just – how is this supposed to derail Sam’s suspicion?”

“Well, at dinner we’re going to be showing him that we’re still best friends – who aren’t sleeping together.” Dean explains. “And that there’s nothing for him to be suspicious about.”

“Sam is coming to dinner too.” Cass says slowly.

“Yeah.” Dean says. “It’s gonna be like a Team Free Will bonding sesh.”

“Where we all sit and lie to each other.” Cass comments drily.

“You know why I don’t want Sam to know.” Dean remarks.

“No, I don’t, actually.” Cass returns. “You said you didn’t want him to know and I respected your wishes. You never gave a real reason why and I never asked because you’re the one doing me a huge ‘solid.’”

“I know Sam.” Dean says. “If he get a whiff of this he will _latch_ onto us. We’ll never be able to spend another moment together without Sam thinking that we’re doing something. And that’s the best case scenario. Worst case? Sam freaks the fuck out and blames me for taking advantage of you.”

“I don’t think-” Cass breaks off as Dean talks over him.

“He’s been chill so far, but that’s only because he isn’t totally sure.” Dean explains.

“So if Sam known then he’ll think that either we’re in love or that what we’re doing is unhealthy?” Cass confirms, seeming put-off by either possibility.

“Yeah.” Dean says.

“Okay. We’ll do dinner.”

…

They’ve dimmed the lights, put on their FBI suits and are currently sitting at the map table with Chinese food just waiting to be eaten.

Sam seems amused by the set up and Cass is just twirling a noodle around his finger before sucking it off.

Like _that_ is helpful.

“Guys.” Dean says to get their attention. “We’re supposed to be bonding.”

“We’ve bonded for over three decades Dean.” Sam snarks. “I think we’re fine. And you and Cass have your ‘more profound bond’ so there’s really no need.”

“Don’t say it like that.” Dean protests, taking his anger out on his pork. The purpose of this dinner is to make Sam _less_ suspicious, not more.

Cass just chuckles and continues playing with his food.

Now there’s an idea. “What about you and Cass. You guys could bond.” He tells Sam.

“Dean.” Sam states in exasperation. “We’re good. Right Cass?”

Cass nods.

“Dude.” Dean whispers. “You’re supposed to be helping me.”

“I don’t know what to do!” Cass whispers back in panic.

“Talk. Speak. Throw some food.” Dean begs. “Anything!”

“Sam.” Cass says brightly. “Would you like some of Dean’s pork?”

Sam snorts even as Dean snatches his box away. “The audacity of some people.” He whispers, cradling the thing.

“It’s a fun team exercise.” Cass argues. “Sharing.”

“I’ll share with Dean.” Sam says immediately. “Here is the broccoli.”

Sam dangles the soggy green thing in front of him and Dean just back away. “I know what to call the Sam-Cass bond.” He says testily. “It’s ‘a brotherly bothering bond.’”

They laugh.

Then Cass slurps another noodle off of his finger.

“Man!” Dean exclaims. “What are you doing! Don’t you chew?”

“I don’t need to.” Cass replies.

“But how does it come out?”

“It doesn’t.” Cass replies evenly.

So that means those constipated looks might actually be constipation. Dean has a field day with that, diving into the mechanics of angel digestion. Cass is surprisingly animate about it.

When Dean looks up to bring Sam into the conversation, he finds his brother’s seat empty.

His watch tells him that over three hours have passed.

What a smashing success this has been.


	13. I’m But A Lowly Gardener, Your Love; My Most Tended Crop

**Summary for the Chapter:**

> Here we find the seedlings of plot growing out of the porn. *bow stage exit left*

Dean finishes dinner with Cass, though the meal now holds a more somber tone. He actually sees Cass chew some of his noodles.

As soon as they’re done though, he asks Cass to clean up while he talks to Sam.

He knocks on his brother’s door feeling like a complete shit.

When Sam opens the door, Dean can tell that he was asleep. Sam leans against the door, suppressing a yawn. “What’s up Dean?”

“Can we talk?” he asks, getting straight to the point.

“Now?” Sam pouts at him, bringing on the puppy eyes. He’s probably looking forward to jumping back into bed.

“Now.” Dean reaffirms. If he doesn’t do it now, he’ll probably never have the guts again.

Sam’s a little more awake now that they’re inside and the lights are on. “Dean… if this is about dinner, it’s fine. I was just tired.”

“It’s not fine.” Dean murmurs, feeling terrible. “I made this big hubbub about ‘team bonding’ and Cass and I sort of cut you out.”

“You didn’t cut me out.” Sam assures.

“Yes we did.”

“Well, maybe you did, a little.” Sam says. “But I _don’t_ enjoy listening to Cass talk about where the stuff he eats goes.”

“And you think I do?” Well, he did. What? Angel digestion (or lack thereof) is fascinating.

Sam gives him a knowing smirk. “Let’s not kid ourselves Dean… you were _enthralled._ ”

“But-”

Sam cuts him off swiftly. “No buts, Dean.” He says gently. “I know that you and Cass are closer than me and Cass are, and I’m fine with that.”

He silences Dean’s protests once more. “We all have stuff we like doing with particular people. If I’m having a night out or wanting someone to talk to, you’re my guy. Some things you just need your brother for. And I know that there are times when you’d rather I be around than anyone else.”

Dean feels his heart swell, it’s nice to be useful. Sam’s right too, sometimes he’d rather his presence over anyone’s – even Cass’.

“But there are some things I don’t want you around for… and that you might not want me around for.” Sam continues. “Sex, obviously and gardening. That’s when Cass and I get to talk each other’s ears off.”

“What?” Dean breathes in shock. Since when have Sam and Cass been gardening? Dean _has_ been seeing a lot more fresh fruit and veggies around the house, but he just ignored them on principle.

Sam nods. “It’s a recent thing, but it’s something we both enjoy doing together.” Dean feels a little jealous. But Sam is right, there are just certain people you want for certain things. “So you understand? I wasn’t mad, or sad, or feeling left out. I just realised that the two of you needed some time to do the things Dean and Cass enjoy doing together.”

…

Dean sags into Cass’ shoulder as he opens the door. “Sam’s fine.” He mumbles into his shoulder.

Cass sighs in relief. “Good. I wouldn’t want things between you two to change because of this.”

“He was nice about it. Gave me a speech about wanting different people for different things. Speaking of which.” Dean raises a brow. “Gardening?”

“It’s nice.” Cass defends. “It lets me feel useful.”

“Come on, you’re plenty useful.” Dean tries to comfort him. Evidently, Cass really believes that he’s useless.

“Let’s be real Dean.” Cass says drily. “My powers are no longer what they used to be. I’m more useful to Sam in the gardening, healing the plants when he forgot to water them than I am to you in battle.”

“That’s not true.” Dean argues. “I need you more than the plants. And that makes you useful.”

Cass smiles. “It’s always nice to be needed.”

“But seriously though Cass.” Dean says, “On the field, you and Sam are the only ones smart and capable enough that I’d trust to guard my back.”

“I know Dean.”

“Some people find men who get dirty to be quite attractive.” Dean comments. “When I’m through mentoring you… you should definitely use that to score some points with the fine ladies and gents of the planet earth.”

“Is this something that you enjoy Dean?” Cass wonders, inquisitive as ever. “From what I know of your love-making style – both in person and from what I’ve read from Chuck’s books –”

“Hold up.” Dean screeches. “You read that?”

“Of course I did.” Castiel replies as though it’s common place to read about your best friend having sex. “All the angels were mandated to read it.”

Ah. That makes more sense than Cass randomly scrolling through Chuck’s works.

“What were you saying then? About my… style.”

“You have a very rough personality.”

Way to butter me up, Dean thinks.

“The angels expected your love-making style to reflect that.” Cass looks oddly nostalgic. “It was surprising to find that you were a tender lover.” Dean shudders at the way Cass says ‘lover.’ “You were always caring and seemed to enjoy giving up control – much unlike real life.”

“And that’s … good?”

“I like it.” Is all Cass says. “You like pleasure, Dean, and you like it when your partner enjoys it as much as you do. That’s impossible _not_ to like.”

Dean’s throat feels clogged, overwhelmed by this unnervingly accurate introspection into the way he has sex. It’s true, of course, but slightly off-putting that Cass knows so much and is confident about saying it.


	14. Tantalizing

Dean raises a brow and pasts on a cheeky grin to hide his surprise. “Oh?”

Cass chuckles. “Now isn’t the time to be shy Dean.”

“I’m not.” He argues, feeling his face flush anyway. Cass grins at him, clearly preening now that he has the upper hand.

“That’s why I always wondered why you seemed so intent on focusing your attention on me during our interactions.” Cass cocks his head to peer up at Dean. “At first I attributed it to your inexperience with men. Then I presumed it was because you didn’t want Sam to know. Then –”

“Wait.” Dean interrupts him. “It _is_ because I don’t want Sam to know. And not damaging our friendship of course. But we solved those problems; there’s no more ‘then’s”

Cass almost pouts at him… and it looks way more adorable than it should. “Of course you don’t want Sam to know since this would be strange for you two and I respect that. Though I still don’t understand it I would never intentionally reveal anything. But you have to admit, it doesn’t cover everything. If Sam does find out he won’t have any way of gauging your level of participation. He’s more likely to assume that you _have_ been participating. You know this.”

With a huff, Dean turns to stare away from Cass. He’s making a lot of sense, which really scrambles his brain. Dean hopes he can get his thoughts together to argue this out. Sam would believe him. Not participating would have made him feel better about the whole ordeal.

Inevitably, as he ponders his response, his gaze lands on Cass’ bed… because it takes up most of the room, not because Dean’s thinking about the good times they’ve had on it.

“I agreed to… mutual satisfaction.” Dean grits out finally when the silence begins to stretch. He doesn’t know why but the direction this conversation is taking is giving him chills and a dry mouth. Which is kinda counterproductive if Cass wants to squeeze in some quality kissing.

“So why are you bringing it up?” Dean asks when Cass remains silent.

The angel just shrugs. “I was just thinking out loud.” He murmurs. By the far away tone of his voice he’s still thinking… and Dean needs to put a stop to that.

What other reason could he have for making their first few sessions all about Cass? It was a culmination of all the stuff Cass said before, nothing else to it. He doesn’t get why Cass is psychoanalysing it. It’s in the past anyway.

“Just to be clear.” Cass still has that inquisitive look. “Why _did_ you agree?”

Dean breaks out in a cold sweat. “Y-you made me!” he blurts. “You just kep-kept asking so I gave in.”

“Yes, but what was your thought process?” Cass hedges.

Dean feels personally attacked. If Cass keeps poking, Dean is afraid that he will burst something inside him that can’t be patched up.

So he does the only thing he’s sure will shut the angel up… and hopefully dash all those disturbing thoughts from his mind.

Grabbing Cass’ face, he swiftly presses their lips together. There’s a beat of protest at first, where Cass tries to continue with his train of thought. But Dean isn’t having that. If he can’t kiss the living daylight out of someone so that they forget everything, then what good is he as Cass’ instructor?

Turns out he doesn’t have to stress about that, because after a few seconds – some of the longest seconds of his life – Cass finally melts into him, his lips becoming pliant under his own.

When he breaks away for air, Dean finds himself forgetting the reason he kissed Cass in the first place.

“Dean.” Cass says surprised, he grins at Dean cheekily and clutches his arm. “Did you just kiss me to distract me?”

That’s when all the blood races to his face. Dean would pray that the darkness is hiding his flush, but knowing Cass, he’d probably hear his prayer and laugh.

“I did not.” Dean splutters indignantly.

Cass just keeps up his amused smile. It gives Dean chills. The angel looks almost pleased by this development. He doesn’t get why he isn’t mad. Dean would be if someone used their charms to distract him.

“I liked it.” Cass says at last, his voice is tantalizing.

“What?”

“It’s like I was saying.” He says. “What was your thought process Dean?”

Should he answer that? _Does_ he even know how to answer that?

“I wanted you to shut up.” Dean explains. That sounds safest.

“And why did you want me to shut up Dean?” Cass asks brazenly.

Hmm. That’s a good one. Dean wanted him to shut up cause he kept asking questions that annoyed him. No, they didn’t so much annoy him as make him unbearable uncomfortable. But why is that? And what had possessed him to kiss Cass out of the blue like that.

He’s wanted the angel to shut up on other occasions too. Then, he either said something wildly inappropriate or just walked off in a huff. Either one of those would have been sufficient here… but Dean had _chosen_ to kiss Cass.

Which is wrong. He shouldn’t kiss Cass for selfish purposes. What they’re doing is a friend helping out a friend. But their arrangement seems to be blurring certain lines for him. He’s starting to confuse Cass with an actual partner and if Dean is honest with himself… he kind of enjoys it.

Having a warm body next to his without needing to be on constant alert in case he picked up with a creature who wanted to murder him is _nice_. The way Cass treats him when they’re intimate is _exactly_ what he craves. When they’re together, it’s a give and take. They’re friends so all the embarrassment with the mechanics of things can be played off with laughter. Cass is insistent where he is pliant, shy where he is bold, and both are inexperienced in their own way – Cass with sex and intimacy in general and Dean with males.

So far it’s not as strange as he thought it would be.

Cass is right, Dean is ‘gentle’ when having sex. It’s not something he thinks should be violent – like every other aspect of his life is – it’s something he enjoys. Cass gets that, which is possibly why Dean falls into a lull like this so easily.

It’s terrifyingly easy to insert Cass is an actual lover. Cass seems to have the same problem whether he realises it or not.

Why else would he be bold enough to bring this up? It’s almost like he’s teasing him, but Dean can tell he takes no pleasure in this. He just wants answers. Answers Dean doesn’t feel comfortable giving.

Despite knowing how wrong it is to abuse their deal like he had - Dean can and probably will hate himself for it later – he can’t bring himself to forgo the feeling of being unbearably, tantalizingly… close.

**Notes for the Chapter:**

> Cass sure does have a LOT of questions ;)
> 
> Next time we'll see if Dean decides to answer any of them or if he's going to try a new method of distraction (one a little more tantalizing than kissing 0:)


	15. Drive Me Bananas

“I wanted you to shut up cause this is weird.” Dean says at last. “This entire thing is weird and screwed up and for some reason you keep wanting to talk about it – clarify some detail that ultimately means nothing.” Dean tugs at his collar, suddenly finding himself hot. “What’s it to you anyway? I _agreed_. Things are going great. Why do you keep asking?”

When Cass looks at him next, his eyes are vulnerable. “Because I’m feeling the same things you are, Dean.”

That shocks him into silence. “I’m feeling… doubt. I feel bad about using you like this even though being with you feels electric. I keep asking you because I’m hoping that I’m not the only one who feels this way.”

It’s not a shock. Really, Dean should have expected this. Cass, after all, is less accustomed to human things than he is. Dean is a master of casual sex and still, he finds himself grappling with the barriers.

“How do you feel?”

“Comfortable.” He says bitterly. “I feel like this is –”

Cass presses his hands to his head in frustration. “When you kissed me just now, I liked it.”

“It was supposed to distract you.” Dean reminds him, his own voice wavering. He doesn’t want to talk about this.

“But it shouldn’t have!” Cass shouts, flinging his hands up. Dean is thrown off by his response to this. Cass is generally calm, less prone to temper tantrums than Dean is. “What we’re doing is not supposed to affect our friendship.”

“It isn’t.” Dean insists. “You’re still Cass. My best friend.”

“The one you kiss when you want to shut him up.” Cass glares at him.

Swallowing, Dean tries to think of a rebuttal. However, nothing comes to mind. Obviously, Cass notes the panic in his eyes and relents, resting a friendly hand on his shoulder.

“I have feelings for you Dean.” His voice is choked. The meaning is abundantly clear. “ _Real_ feelings.”

“I look at you and I think about us in bed.” Cass continues his tangent, his eyes wide and panicked. “I see you in the kitchen and want to tease you about something you said this morning but Sam is there… and he’d wonder why you were in my room. When we’re sitting somewhere, I find myself leaning closer, smelling you, wanting to lick your lips.”

In stunned silence, Dean just stares at him as he begins to pace.

“I kept asking you these things because I was…” he swallows, pausing his pacing to look over at Dean nervously. “I was hoping you felt the same way.”

He doesn’t know what to say to that. “We… we crossed some major lines Cass.”

“But are you handling it as well as you pretend to be?”

“No.” Dean admits. “Separating… this from our normal interactions is hard. I like this too Cass.” He divulges. “Way more than I thought I would. I like being in bed with you, waking up to you when I fall asleep. I like that I can show you things and let go with you.”

Relief shows on Cass face. “I like it when you fall asleep… I get to watch over you all night. I enjoy being with you, knowing that I’ve tasted your lips and that you trust me enough to do this with me. Despite your… inexperience with men, that you’re so eager to do this with me. I love touching you. Watching you moan and whimper and knowing that _I_ made that happen.”

Dean’s breath hitches, he feels his eyes dilate with lust. “It’s not just about teaching you anymore.” Dean confesses softly. “You’re right. I enjoy what we do. It’s become less of a challenge. I’m actually _excited_ when you knock on my door and I feel like shit because I’m supposed to be helping you.”

“But if we both feel this way…” Cass lets the statement hang but the hopefulness in his voice is hard to miss.

For a moment, he considers what could happen if they just accept this. Complacency is never a good thing… but this is something that makes them both feel good. Nothing would change really. Their friendship would be as strong as ever. The only difference is that they’ll both acknowledge that they make each other feel great.

“We both feel this way…” Dean confirms. “…and it doesn’t have to be a bad thing.”

It just means that they’re on the same page, that they can be more open.

Cass’ lips are on his own in an instant, pressing against them in a way that has his lips opening up to accept Cass’ tongue. Sagging into their embrace, Cass lets Dean take control, knowing that he’s confident in this skill after all the times they’ve kissed before.

“Mhh.” He moans against Cass lips. Dean places his hands on Cass’ shoulders to steady himself. “So good.”

“Dean.” Cass whispers against his lips. “I want to try something.”

“What?” Dean moans, his mind still foggy from the kiss.

“I want to try fellatio.”

Well that sobers him up quick.

“Now that we’ve established that this… thing, is no longer just about teaching me, I want to try this.”

Dean doesn’t know how he feels about blowing a guy. After the first time they brought it up, Dean had done some checking. About technique and speed and suction. The thought of having something in his mouth is a bit degrading. It’s Cass and he knows he won’t use it against him but Dean can’t shake the feeling. But he can’t deny that something in him flipped at the thought of it.

“I guess.” Dean says. “You know, it’s my first time doing this right. So um, don’t get your hopes up.”

Cass just frowns at him, bewildered. A few seconds later, realisation slackens his features. “Oh.” He says. “Well… I wanted _you_ to be on the receiving end.”

…

At Cass’ insistence, Dean finds himself sitting on the edge of the bed, his pants around his ankles, his shirt cast somewhere across the room and a tomato red flush covering his body. Cass is on his knees before him, his own suit and coat combo in disarray from Dean’s tugging. He’s lucky that nothing ripped. He knows how attached Cass is to his holy tax accountant get up.

Nerves has his hands fiddling with the bedsheets as Cass stares up at him with big blue eyes.

“I’ve studied extensively.” Cass assures him. “I practiced on a banana but I was unable to gauge it’s level of satisfaction after the tip almost broke off in my mouth. I’d have died if I were human.”

Dean laughs, killing the romantic mood… but how could he not? This is hilarious. Cass deep throating the banana so far it broke off. Dean hopes – for his dick’s sake - he’s at least aware of the no teeth rule. Cass gives him a shy smile as his laugh tapers off.

“The tip of my dick won’t break off.” Dean assures.

“Good to know.” Cass says morosely, giving him one last look, as though sizing him up.

Then he swallows Dean whole.

It’s so unexpected that Dean almost jerks in surprise. Cass stays seated, his lips closing securely around him. He pulls off slowly, dragging a groan from Dean as he struggles to remain still. His lips linger around the head, his tongue poking out to lick at Dean’s sensitive flesh. Most of the blow jobs he’s gotten have been hard and fast, against a wall or in a bathroom stall. Rarely did he ever have an actual bed.

He whimpers obscenely as Cass’ tongue stabs at his slit. The angel increases the suction until Dean is gasping and writhing, his legs drawing up to, wanting to torque his hips up to get closer to the pleasure.

“Cass.” He moans. It’s a silent plea for more.

Cass doesn’t listen, content to suck on his head like a goddamned lollipop.

His eyes flit up to Dean’s face, and he feels himself tremble at the intense visual. Now that he’s mentally accepted that this is something he enjoys, it makes him experience the sensations that much more intensely. He can appreciate Cass’ touch and show it. It makes things even hotter than usual. Then, of course, there’s the matter watching Cass’ sensually suck him that has him aching for more.

“Please.” He begs.

With a loud pop, Cass releases his cock, using his finger to stroke the length of it. “I bet you’re jealous of the banana now.” He teases.


	16. Like a Bazooka

“Yes.” Dean pants. “Yes. I’m jealous of – of the stupid banana. Just keep doing that.”

Cass looks up at him smugly. “Okay.” He says before covering Dean’s cock slowly. One of his hands is resting on Dean’s hip bones, mostly to keep him in place and the other is playing with his balls.

Dean has no choice but to shut his eyes against the onslaught of pleasure.

It’s almost too much, Cass lips wrapping around his sensitive cock. The taboo of it all makes it even hotter. Cass is his best friend. His _guy_ best friend. At the start of this ‘help Cass out’ initiative he thought his cock would object solely because Cass was male. That hadn’t been the case. Stimulation is stimulation. Plus, they both agree that they’ve come to enjoy being together like this.

A fact which still rattles Dean.

This visual; Cass on his knees, licking at his cock like it’s a friggin popsicle, it turns him on like no other. He squeezes his eyes shut as Cass laves at the tip, purposefully teasing him.

“You taste delicious.” Cass murmurs, his words sending vibrations straight down his dick. There’s a touch of surprise in his voice too, as though he hadn’t expected to like it.

“Giving you this pleasure, it seems to be an aphrodisiac for me as well.” Leave it to Cass to get all philosophical in the middle of sucking his dick. The angel gestures to his tented pants.

“I’ll take care of it.” Dean promises, reaching out to stroke a hand through Cass’ hair.

“I know.” He says, sweetly, his eyes lighting up before leaning down to give Dean's dick all the attention it needs.

With a hand resting on the side of Cass’ face, he groans, pressing his head back.

Cass really seems to be enjoying this, which comes as a surprise. It’s rare that he gets a nice, slow blow job. Then again, this isn’t some dark alley and Cass isn’t some chick who’s half drunk.

“So good.” He moans as Cass continues his licking. He moves up and down, making Dean’s head swirl with pleasure. His tongue does all the right things making him shiver deliciously. His actually terrified of blowing his load too soon.

Cass’ hands don’t remain idle, he strokes up Dean’s legs, squeezing at his hips, both holding him in place and turning him on even more. Half the time his eyes are closed from the pleasure, but Cass’ hands are there, grounding him, reminding him _who_ is doing this to him and why.

Then he pushes further and Dean’s eyes fly open as his sensitive head hits the back of Cass’ throat. “Holy shit.” He gasps, his hands weaving into the angel’s hair. With a smug look, Cass swallows around him, his eyes twinkling up at Dean.

They keep the rhythm, Cass moving his head up and down, making sure to knock Dean’s head on the back of his throat with every single thrust. He manages not to moan to loudly by using his sheer force of will… and the thought of how mortifying it would be to have Sammy break down the door, thinking that he was dying or something, and find them like this. He would _really_ die then.

“I’m close.” He grits out, struggling to keep himself still.

Cass just cocks his head, which presses Dean’s dick against the side of his mouth.

Dean lets out a breathy laugh, feeling his dick twitch at the change in sensation. “Dude. Means you can pull off and I’ll finish with my hand.”

With a loud pop, Cass pulls away from him, leaving his spit covered dick to rest on his stomach. He doesn’t try to move and Dean feels pretty weird jerking off with his face _right there_ , but what the hell? He’s desperate to come after that blow job.

However, when his hand tries to wrap around his dick, Cass smacks it away and cocks his head once more. “Was I not doing a good job?”

Dean’s pleasure riddled brain takes a second to absorb the words.

His brows raise and he gapes at Cass. “Man you were perfect. You did everything right.”

 _Sucked my soul out through my dick_. Dean thinks to himself.

“Then why didn’t you let me pleasure you?” The question is so innocent that Dean’s brain takes a moment to figure out what he really means.

“Oh!” he says sharply. “Well… it’s um, polite?” Is that the right word? “To warn the person who’s sucking you off when you’re about to come.”

“But…” Cass’ confusion is evident. “ _Why_?”

“So you don’t get a mouthful of come that you’re not ready for.” Dean says crudely.

“I don’t mind.” Cass says evenly, giving his dick an interested glance. Dean gives him a look, wanting to make sure that he’s really okay with it.

Dean sucks a sharp breath. “O-okay. Go for it then.”

His words only make Cass more determined, he moves a little faster, sucks a little faster. One more swipe of his tongue and Dean is a gonner. He comes with a shout, his legs thrashing and his hands yanking at Cass’ hair. The angel tongues him like a pro throughout his orgasm, gently slowing the pace as Dean comes down. When his vision is no longer double, he glances down to Cass whose lust filled eyes are staring at him, drinking in his blissed out expression.

Dean’s eyes flit to his throat as he swallows.

 _Swallows_.

It gives him a thrill, that some part of him is inside Cass. Soon to be expunged by the angel’s ‘digestive system,’ but there nevertheless.

“Was it good?” Cass asks his voice sounding surprisingly jagged.

With a scoff Dean lays a hand on his shoulder. “You just made me come like a bazooka. I think you get an A+ in the art of fellatio.”

Cass beams at him before sliding up to join Dean on the bed. With a wink, Dean lets his hand trail down, cupping Cass through his pants. There's already a sizable wet spot. And even though he just had an orgasm, Dean feels his dick twitch as he takes note of just how much Cass enjoyed sucking him off.

“My turn.” He says as he fiddles with the zip.

**Notes for the Chapter:**

> Some smut and minor feels. Next up: let's see how Dean does ;)


	17. Go Bananas

**Notes for the Chapter:**

> Sooo before we dive in.
> 
> Y'all know I have like tonnes of works that I update. My biggest fear is that I put a chapter in the wrong place.
> 
> This one almost went into Baby in a Trench-Coat... which would have been confusing affff
> 
> BUT thankfully, I caught it haha.
> 
> So enjoy and go bananas!! (as we hope Cass will)

Oh God, he’s really doing this. Dean lets out a sharp breath. His hands fumble with the zipper in a very un-Dean-like manner. His mind is racing. Trying to remember the things _he_ likes in a blow job.

Well lots of moisture for sure. But Dean’s mouth feels as dry as a desert right now, nerves sapping up all of his spit. Uh, water! He needs water. He reaches into Cass’ pants to release his cock. It feels familiar in his hands, which really speaks to how much they’ve done together.

Uh, Dean likes lots of tongue. No teeth. Um, deep-throating… which Cass had done like a pro. He isn’t sure he can get Cass’ dick that far without gagging and choking in the most embarrassing way. But then Cass won’t know it’s embarrassing cause he hasn’t done this before.

However, the angel _has_ done lots of research. So maybe he _will_ know how horrible Dean is. Maybe he’ll just decide to end things after Dean chokes on his dick like some noob.

Research… now there’s an idea.

But it’s not like he can run to the bathroom with his phone while Cass is here like this.

“Hey, Cass?” His voice comes out unnervingly high. _Cool it Winchester_ , he reprimands.

“Yes, Dean?” his voice is breathy and low. He really isn’t paying attention.

What Dean is about to do will kill the mood – for now. It’ll be worth it though. Making a fool of himself while sucking Cass’ dick won’t do wonders for the mood either. At least this way he can go in with _some_ sort of knowledge.

“I’m thirsty.” He says. “Can you grab me a glass of water from the kitchen?”

Dean winces as the words leave his mouth. That sounds just as bad as it had in his head.

Clearly thrown off, Cass freezes. “Um…”

“Just a glass of water.” Dean coaxes, “And maybe Cas-a Erotica.” He adds with a wink. There at least Cass will be taken up for a few minutes.

The angel gives Dean a strange look as he sits up. “Of course, Dean.” He says gently.

Dean gives him a tight smile and awkwardly watches as he tucks himself into his pants.

As Cass lingers near the edge of the bed, he turns and rests his hand on Dean’s knee. “You know, you aren’t obligated to ‘return the favour.’”

“I know.” Dean says quickly. He doesn’t want Cass thinking that he doesn’t want to do this. He does. Sort of. It’s just that he wishes he was more prepared. But asking for a banana to practice on at this stage is out of the question.

“I want to.” He assures him, patting the hand on his knee. “I just need that drink. And the porn.” He adds as an after thought. “You know, to set the mood.”

“Oh.”

Dean manages to sit still as Cass makes his way out of the room. But as the door clicks shut he flings himself over to the other side of him bed and fumbles with his phone.

Mind racing, he tries to punch in his password… which does not work out well. Frustrated, he tries again, thankfully getting it right. He has to hurry. Cass will be back any minute now. Shakily, he lets out a breath and stares at the empty search bar.

Okay. Whatever in inputs needs to be precise as hell.

Uh… _How to suck dick like a pro_

No. He backspaces that immediately. _Top ten tips for giving a blow job_

Dean hits enter and swallows as a whole bunch of articles pop up. It seems like they focus on when the _girl_ is doing the blowing. But Cass blew him just fine.

It’s only fair that he at least try to do the same.

Oh God, the door knob is rattling and he hasn’t even made it past step two. He chucks his phone under the bed hoping that Cass is too distracted to notice the glow.

“I got the water.” He says. “And the porn.”

“Good man.” Dean says, clapping him on the back as he walks over.

Cass still looks uncomfortable though.

“What?” Dean asks, already fearing the worse. What if Cass has decided to end it, now that feelings are in play. No, he seemed to be relieved when Dean admitted it. What if-

“Sam saw me.”

With a sigh of relief, Dean releases Cass’ shoulder. “Dude, you almost gave me a heart attack.”

Cass frowns at him. “Sam _saw_ me.” He repeats. “Like this.”

One sweeping gesture draws Dean’s attention to Cass’ very visible hard on.

Suddenly he’s choking on his spit. Cass slaps him rather harshly on the back.

“He didn’t suspect anything did he?” Dean asks as he catches himself.

“I don’t believe so.” Cass says. “He just recommended that I not borrow porn from you.”

“Oh, uh, and what’d you say?” Dean wonders as he pops in the porn.

“I said that you have impeccable taste.”

Not great, but not the terrible either.

“Good work.” Dean says, taking the glass.

“Thank you Dean.” The way he says ‘Dean’ in such a low tone almost has him choking on his water.

The water does help, but as he gulps it down, the fact that he’s about to suck a dick becomes very real.

Cass is leaning against his headboard, watching him very carefully. Casa Erotica is playing in the background but Cass’ focus is solely on him.

So Dean just smirks up at him and touches the top button of his pants. He gives Cass’ cock a couple strokes, just to get it nice and firm and then he licks the tip, watching Cass like a hawk to gauge his reaction. It looks like he’s enjoying it. His head is tipped back, eyes squeezed shut; so Dean keeps up the little licks. Slowly easing himself into the idea.

The taste isn’t too bad. Kind of tangy.

Dean shifts himself so that he’s crouched right between Cass’ legs. He does a quick bob down and then lifts back up. He hears a kiss and notices Cass’ eyes cracking open to look at him. The blissed out look in his eyes prompts Dean to do it again.

This time he gets a broken off moan for his efforts.

That’s when he realises… it isn’t what he thought it would be. It doesn’t feel demeaning or gross. It feels… nice. He likes that he can coax these noises from Cass.

The way he moans Dean’s name is purely _erotic._ The noises from the film playing in the background don’t hold a candle to Cass’ sexy whimpers. Go he moves faster, a little deeper. And he gags.

With a gasp he pulls off and presses a hand to his mouth.

Cass gives him a crooked smile. “You don’t have to do that.”

“But you did.” The words are out of Dean’s mouth before he can stop them.

“We’re different, Dean. I have no gag reflex.” Dean tries to protest him but Cass shushes him. “No. What you were doing before was perfect.”

Dean gives him a dubious look, but continues his ministrations.

Turns out Cass wasn’t lying. Just a couple more strokes and a few flicks from Dean’s tongue and his hands are scrambling over his head and shoulders, his legs drawing up as he explodes down Dean’s throat. Dean holds himself steady, relaxing his throat so that he doesn’t coke on the sudden influx of cum. Cass moans and twitches as his cock kicks in Dean’s mouth.

“Dean.” He whispers as he comes down.

He releases Cass’ cock and runs a finger down its length, causing Cass to shiver from the sensitivity.

“That – that –” Cass swallows. “Dean that was perfect.”

Blushing, Dean graciously accepts the praise. He won’t admit how scared he was beforehand, but he’s glad that Cass enjoyed it.

“Don’t mojo it back up.” He says softly, moving up to press a kiss to the angel’s lips. “Enjoy the afterglow with me.”


	18. Undeniably Electric

**Notes for the Chapter:**

> Hey everyone!!
> 
> I hope you like this chapter.
> 
> I'm sorry I haven't posted much recently, my laptop is broken and I won't be getting another one for about a month. I'll keep writing on my phone but updates will probably be slower because typing is harder on my phone. I'll do my best though.
> 
> <3

Of their own accord, Dean's eyes keep drifting to Cass. The angel looks wrecked - in a good way. His hair is messed up, just like back in the day, and his body is slack on the bed.

_ You look so beautiful like this. _ Words Cass said to him once… but could now be easily applied to the angel.

Blissed out, on his bed. Dean can't help himself, he's entranced.

He almost can't believe that he had a dick down his throat. But the tangy taste that lingers in his mouth cements the experience.

As he slowly comes off of his own high, he suddenly remembers what occurred before the 'fellatio'. The things they divulged. A shot of fear runs down his spine, swiftly chasing away any laziness from his orgasm.

His next breath stalls in his throat as he remembers the things he said… the lines he crossed.

Feelings.

Of course he has feelings… how could he not? Cass is the perfect partner. He insists that Dean give him as much pleasure as he gives Cass, he always makes the right noises and touches the right spots.

Perfect.

But Dean wasn't supposed to  _ tell _ him that. Feelings would screw up their friendship. Dean swallows tightly. Would he buy that his confession had been as a result of some spell or potion?

No.

Dean was too sincere. His 'feelings' are out there now. And he is terrified.

Which Cass picks up on, the moment he opens his eyes.

"Dean." He says, sitting up, his voice sounds strangled. "You regret it."

The resignation in his voice and the accusation in his eyes makes Dean shivver. It's almost like Cass expected this. Of course he had. Sometimes Dean thinks that the angel knows Dean better than he knows himself.

But  _ does _ he regret it?

That could easily have been the most pleasurable encounter of his life. 

"You regret this." Castiel repeats morsley, as though wrapping his head around the idea.

"No!" The words are rushed, "this was great, Cass. I-I don't regret it." Not really, any way.

Dean allows himself a deep breath before locking eyes with Cass. "We just said some stuff." He says weakly. "Stuff that… that friends don't say."

Understanding replaces the sadness in the angel's expression.

"You're referring to our feelings." Cass concludes with a nod. "Human emotion is a complex thing. Do you think, in light of what we've just done, that you may have misinterpreted or - or perhaps not conveyed your feelings aptly?"

Cass sounds so sage, like whatever Dean decides on, it'll be okay. But this is someone Dean has known for many years. He knows almost every one of Cass' expressions - he knows that look in his eye.

He's putting on his brave face. Giving Dean a chance to walk away despite how much it would hurt. In his worry, Dean had forgotten one important detail: he wasn't the only one to show his hand tonight.

Cass took a big risk too, telling Dean about his feelings. Dean could have scrapped their entire deal then and there. And he knows that Cass knew that going in. Yet, he did it anyway.

The angel bared his heart and Dean had done the same. How can he cheapen that moment with a lot?

He blows out a breath as his decision becomes clear. It's going to change things between them… but Dean is sticking to his guns.

"No." His voice sounds surprisingly confident. "I think the message got across just the way I wanted it to."

The relieved smile that softens Cass' features causes his lips to twitch.

"So we both have feelings." Cass reiterates. Dean hears his words as though in a daze.

He nods.

"Does that mean we're together?"

Dean almost chokes in his shock. Leave it to Cass to go from zero to one hundred in one second flat.

"Honestly?" Dean tries and fails to keep his voice even. "I don't know if that's the right term. I do see you differently now, but at the end of the day this is still me helping out a friend. This is still new - our feelings are still new. I still feel doubt and worry but the electricity between us is undeniable." He lays a hand on Cass' arm, hoping to soften the blow.

A contemplative look creases Cass' features. "Since you've been honest with me, it's only fair I return the favour."

Dean quirks a brow, wondering what Cass means by that. He doesn't have to wait long, because Cass looks at him with doe eyes, his face drifting closer.

"You say our feelings are new, but that just isn't true." Dean sucks a surprised breath, his mind almost shutting down at the implication.  _ Your _ feelings may be new, mine however, are not."

Dean's heart stutters at Cass' vulnerable expression. Once again the angel is putting his heart on his sleeve, baring his soul for  _ Dean. _ The man who sucks ass at expressing his emotions in a healthy way. Cass trusts him with this.

That alone emboldens Dean to keep his cool. On the inside his mind is exploding, his heart racing as everything from the last few years comes crashing into him like a tidal wave, drowning him in everything he was oblivious to before.

But on the outside, he keeps his expression relaxed, determined not to freak out.

"I've loved you for years, Dean." 


	19. And Now He Knows

"I've loved you for years, Dean."

The way Cass looks at him then is nothing short of adoring. His fingertips brush against Dean's. He feels lost in their own little paradise, where it's just him and Cass. The intimacy of the moment makes him feel utterly secluded from the outside world. So it takes a few seconds for Cass' words to truly register.

When they do, his breath hitches, causing Cass to look away. The contented expression on the angel's face is replaced by fear. A confession like that…

There's no way it can be misinterpreted.

Dean feels the realisation hit him like a bullet.

_ Cass is in love with him. _

And has been in love with him for years. This is the part where his brain should be short circuiting. But strangely enough, it doesn't do that. All he can think about is the way Cass looked at him as he told him he loved him. He looked scared, but also weary. That makes sense, he'd been holding all his feelings in for years. Letting it all out must have been a great relief.

Years.

How did no one notice?

Thinking back, Dean can see it. The breadcrumbs of love and affection that he'd been to stupid to follow.

Him and Sam both.

A bunch of crazy teenaged fans had seen it and latched on. Him and Sam? The seasoned hunters? Nope. They were as blind as bats.

Dean doesn't know what to say. But Cass isn't done.

Shame lowers his voice. "I've loved you more than a friend should from the very beginning. I thought I could control it -temper it- but it raged more and more out of control with every second I spent in your presence. When I saw the DVD my only thought was that you wanted me back… pathetic, I know, but it's been years Dean. And - and now that I know that the idea of being with me isn't entirely abhorrent…"

Cass trials off with a loud gulp. His eyes can't seem to stay still. They burn with shame and distress. Dean still hasn't wrapped his head around this revelation, but he knows that he needs to say something fast. For Cass' sake.

"So if you didn't…" he trails off uncomfortably, "you know… then you wouldn't have gone along with the whole 'jerk off instruction' thing?"

Dean glances up at Cass, hoping for once, that he said the right thing. However, the angel looks stricken.

All Dean can manage is an undignified stutter as he try to figure out something more appropriate to say. But this isn't his thing.

Sex. That's his thing.

But words? Feelings? He's a disaster when it comes to those.

He feels  _ something _ for Cass. But to admit it to himself… to put it into words… Dean just can't do that yet.

Cass is a dude. Or in a dude's body anyway. It's easier to call Cass his friend. To think of their time together as a friend helping a friend.

It's wrong. Dean knows that. But he needs time to wrap his head around the idea of being a boyf-

_ Boyfriend _ .

The word sends icy chills down his spine.

Cass just shakes his head sadly, as though he can sense Dean's internal conflict.

"It's okay." He murmurs. "And yes I wouldn't have done this if I wasn't attracted to you."

There's a pause. Cass fingers shift slightly, reminding Dean of how close they are. How close he  _ let _ them be.

"Now that you know… do you think you can still be around me? Intimately and otherwise?"

Now that gets him thinking. Loving someone is a life changing detail. Does he feel differently about Cass now? He gives the angel a cursory glance. Still the same ole Cass.

_ Just the angel in the dirty trench coat who's in love with you.  _ A nasty voice at the back of his mind hisses. Dean forces himself to shake it off and focus on what's important: Cass.

After royally screwing up with the first question, Dean is determined to do better with this one. Especially because of how small and timid Cass' voice sounds.

"You wanted to be close. I get it, Cass. It's normal." Dean stresses. Cass blinks at him, letting out a sigh that's equal parts relief and disappointment.

"I - I wanted it too." Dean tacks on softly.

Cass' eyes dart to his, filled with shock.

I mean." Dean rushes, not wanting Cass to get the wrong idea. "I'm still working out how I feel. But I completely get how you must have felt. So um, I don't hold it against you or anything. We're good."

"We're good." Cass parrots, looking down at his lap.

Dean doesn't need to see his entire face to pick out the regret making his features sag. He swallows tightly, unsure of what to do or say to make things better.

He tries to put himself in Cass' shoes. Tries to think of confessing his love to his best friend. Dean flushes, his eyes darting over to Cass'. He doesn't think he'd be brave enough to go through with it.

But Cass had.

He was brave.

And Dean had replied in badly formed sentences. 

_ 'We're good.' _

That's not fair.

Reaching up, he tilts Cass' head to face him. The angel's jaw is clenched and hurt swims in his eyes.

"Cass." Dean whispers.

Once again, Cass becomes tense.

"I'm sorry." He whispers. "I'm such an ass."

Cass scoffs.

"I'm bad at this." Dean continues. "Like really bad. But you know that already."

"I know you don't like males." Cass says, slowly. "You didn't like minute four."

Dean tries to deny it, but Cass just glares at him. They remain like that for some time. Just staring at each other. Then Dean looks away.

"You are not obligated to address what I said Dean. The fact that you haven't fled is enough for me." Cass says gently. But even though his words sound carefully chosen, Dean can still hear the remnants of sadness in his voice. "I said it because you deserved to know the truth… and I was tired of dragging around that secret."

Dean's heart clenches.

Cass thought he would leave after he bared his heart like that. Dean looks down, his fingers playing with the sheet in contemplation. With a start, he realises that they're both still naked.

Naked, in bed, basking in the afterglow together.

Like a -

Shaking his head, Dean lets out a harsh breath. He can't think of that now. But he  _ does _ need to make one thing clear.

"I'm not going to ignore it." He says after a beat. "And for the record, you should never have to feel ashamed about the way you feel."


	20. A Winchester Guide to Becoming Friends With Benefits Without Knowing

"Dea-"

Loud banging silences Cass.

Dean blinks in confusion. The whole reason they chose Cass' room was because Sam was unlikely to come knocking.

Yet, here he is.  _ Knocking _ .

"Hey Cass!" Sam bellows.

With a worried look at the door, one that makes Dean wonder whether or not he locked it after he came back. Cass calls out, "Sam?"

"It's pouring outside. I wanted your help to check our garden." Sam hums in consideration. "Is something wrong though, you're usually waiting for me when this happens?"

"Everything's fine." Cass says in a rush, throwing a pensive look over to Dean.

The strangest feeling tightens around him. It constricts his throat, stopping him from making even the smallest noise.

He just sits there in stunned silence while Cass watches him.

Sam is  _ here _ . His little brother is practically banging down the door. The door that he's not sure they even locked. If he opens that door…

That jolts Dean into motion. He springs up and scrambles over the blanket until he's crouched on the side of the bed. Sam would really have to look to notice him now.

'Go.' He mouths to Cass who seems torn.

His face is so expressive. Dean knows without a doubt what he's thinking right now. So he does his best to assuage those doubts.

'I'll wait here.' Dean mouths.

That seems to do the trick. Cass still looks a bit uncertain but he gives a small smile anyway. "We won't be long." He whispers before standing.

…

Despite his promise to stay put until Cass returns, Dean can't help but feel trapped.

His emotions are running high. From sex. From admitting his feelings. From discovering the true depth of Cass' feelings. And being in this room only feels suffocating.

But if he leaves, Cass might get the wrong message.

What message that is, Dean doesn't know.

Now that he's established that ignoring Cass' feelings is out of the question, Dean has no clue how he's expected to face his friend after this.

When they were both in the 'maybe I might feel something' category things seemed easier. There was still a chance that things would become clearer with time.

However, Cass' feelings are clear. They have been clear for 'many years.'

It's still a struggle for Dean to wrap his head around that.

On one hand, it's taking everything in him to not run screaming. But on the other hand, he can't do that to Cass. He promised that he'd stay… and talk.

What the hell is he going to say? They can't 'get together', that's for sure. 

But maybe…

Maybe they can keep doing what they're doing. Dean isn't the best at romance, but he can definitely try for a few dinners… and blow Cass' mind with some awesome sex.

But he doesn't want to lead him on. He might have feelings but Dean is sure that they'll fade once Cass learns to get off without him and they stop sleeping together.

The easiest thing would be to tell him that. That while he might feel something, things could easily change. Everyone knows it's impossible to sleep with someone this close to you and not catch feelings.

When the door cracks open Dean jumps.

"Dean." Cass breathes as he catches sight of him. "You stayed."

"Said I would." Dean mumbles, ducking his head. He wracks his mind, trying to remember what he was supposed to say.

Seeing Cass now is just… distracting.

"Well thank you." Cass says, drawing closer to the bed.

"How're your plants?" Dean blurts.

With an amused look Cass settles next to him. "The rain did a bit of damage to the smaller plants, but nothing they can't recover from. We… um -" He breaks off, shaking his head.

"What?" Dean wonders. Maybe because he's so eager to do anything but talk about what they're supposed to.

"We picked some of the half- ripe tomatoes. So that the birds don't eat it." Cass finished weakly. "I just - was going to offer one to you. But I know how you feel about vegetables."

To see all that excitement fizzle away physically hurts Dean.

"That's usually true." He says, "but maybe I can make some tomato rice soup?" He offers.

By the way Cass' expression brightens, he knows that he's made the right choice.

"That would be nice."

"It's been a while anyway." Dean shrugs, trying to play it off nonchalantly.

This time, when they break off, the silence is anything but comfortable. "Cass… you know if I knew… that I'd have done things differently right?"

The angel nods.

"I honestly don't know why you picked me, out of everyone. Hell, even  _ Sam'd _ be the better option for you." Dean sighs.

Cass gives him a stern look. "I didn't  _ choose _ to love you Dean. In fact, when it became apparent to me I did everything I could to stop it."

That almost hurts. No, it definitely hurts. And Cass must read it from his face because he shakes his head, "I was an angel Dean, angels aren't supposed to feel these things. I could list a thousand reasons why you're the best option… but I fear that would only 'creep you out.'"

The way he does the air quotes makes Dean chuckle. "You doing that creeps me out."

"I know you don't believe me, but I'm happy it's you Dean."

Cass is right, Dean doesn't believe that. After all his fuck ups, his lies, his callousness… how can Cass love him?

"So about us." Dean feels himself flush just saying the words. "I don't want you reading anything into this. My feelings are new, we don't even know if they're real."

"I know." Cass says, "I don't expect anything from you Dean. I was just being honest."

But this is the dude Dean has known for years. He might not expect anything, but he can tell Cass craves it.

"I'm still gonna be your sex guru." Dean assures. He doesn't want to make a big deal about it and make Cass even more uncomfortable.

"As long as you're always my friend. That's the one thing I couldn't live without."

The sincerity almost breaks Dean's heart. Because he gets it. He can't imagine his life without Cass' friendship. "Me too, man."


	21. Let it Blossom

**Notes for the Chapter:**

> Hey guys! I know I've been gone for a bit. BUT I'm back... and with a fully functioning laptop! So I'm hoping to get back to more regular updates. Thanks so much for being patient. I've absolutely loved reading your comments and hearing what you think!
> 
> (Also... seems there's gonna be a DeanCas date uwu)

Dean falls asleep again. He doesn't even remember it happening. And it's worrying because it's never happened before. Four hours and he's usually good to go.

When he wakes again Cass is staring at him.

Like…  _ really _ staring at him. It’s the way Cass always stares at him. But this time he can really understand the meaning behind it. And damn if it doesn’t make him squirm. Usually he can stare back effortlessly. Because he could feel the connection between them - and he still does - it’s just become overshadowed by Cass’ love.

Now Dean finds it hard to hold his gaze, because he can see the yearning in his eyes. The pull is still there. Dean suspects that will never change, but it just feels different. Strange.

Dean looks away first, biting his lip and hoping that his flush doesn’t show in the darkness.

“You slept well.”

Trust Cass to state the obvious. Yet, Dean finds himself smiling and nodding, still unable to look the angel in the eye.

“Dean.” Cass says, his fingers brushing against Dean. “Are you okay?”

Dean swallows tightly, but finds it in himself to look up and face Cass. The worry on his face is clear. It makes sense. Dean has never done well with emotional revelations. Even though he promised that things are still okay, Cass is probably waiting for the other shoe to drop. For Dean to spiral and fuck up.

But he won’t. He  _ won’t _ .

Not this time.

This is too big a deal for him to screw up.

“Yeah, man.” He assures, running a hand through his hair. “I’m just… processing.”

It’s as honest as he can get without freaking Cass out. He’s  _ processing _ the fact that he feels warm and fuzzy waking up like this, despite the panic brewing in his chest. He’s  _ processing  _ the way that it’s too easy for him to stroke Cass’ fingers to reassure him.

The lines are blurring. The lines are basically gone.

Dean has no way to class this as a friendly act.

He spilled his guts to Cass and point blank confessed his feelings and Cass’ did the same. Except his feelings are real… hidden for the better part of a decade, but real nonetheless. And… that changes things. How could it not? When your best friend admits that they’re in love with you, you don’t just go back to normal.

Or do you? Maybe that’s what normal people do… maybe Dean  _ does _ have feelings, which is why he’s even contemplating this.

It’s too soon though. Too soon to be concrete. He just needs to give it time to fade… or to blossom.

And Dean doesn’t know what option scares him more.

“Can I kiss you?” Cass sounds so shy… looks so vulnerable. 

Kiss Cass… after the night they had, he probably shouldn’t. But he finds his eyes drooping and his body leaning closer. Then Cass’ soft, measured voice breaks through his trance.

“You can say no.” It’s clearly an afterthought to Cass. But to Dean… that thought hadn’t even crossed his mind.

He feels himself flush as his thought process mocks him:  _ Kiss Cass? Hell, yeah. _

Damn it, he should have been thinking about the consequences. About how  _ bad _ an idea kissing Cass after last night is. Yet… his brain had been utterly delighted by the idea of kissing Cass good morning.

Or good night.

The occasion hadn’t really mattered.

Just the fact that he’d be kissing Cass.

Which is… telling.

Straight men don’t fantasise about kissing their ‘best friend with benefits who needs him to get off.’ Then again, most straight men probably don't have a ‘best friend with benefits who needs him to get off.’

But his lips are suddenly on Cass’, savouring the noise of surprise he makes as Dean’s hands thread through his hair, angling his head so that their mouths fit together perfectly. He relishes in the way Cass just melts into him, his lips velvety and lush against Dean’s. He kisses him slowly, languidly, not letting his brain spoil this for him. He parts his lips ever so slowly and runs his tongue against Cass’.

Touching Cass feels so good. His hair is wrapped around Dean’s fingers, his skin is warm against Dean’s palm. It is so good. So much. Purely  _ Cass _ .

And it drives Dean crazy.

He feels little Dean rear his head but Dean doesn't care. Kissing Cass is too heady to stop.

It’s Cass who nudges him away gently, stroking his chest gently as Dean pants. With satisfaction, he notes the pinkness on Cass’ lips and knows that his must be equally wrecked. 

“Well. That’s one way to say good morning.” Cass is clearly trying to play it cool. But the tremor in his voice suggests otherwise. 

It’s insanely hot.

He  _ likes _ turning Cass into a mushy puddle of-

Dear God, what is he thinking?

He’s short of breath for a whole new reason now.

He’s straight. Straight as an arrow. But he can’t deny the attraction he feels with Cass.

Maybe there’s a way he can help Cass feel the closeness he craves while seeing if there’s any spark between them.

Dean considers it for a moment. He was on the right track before… he just tried to make the boundaries clear and avoid suspicion by including Sam. That had monumentally backfired. And now that Sam’s made it clear that he doesn't care if they hang out without him, because he and Cass have their own thing…

“Do you wanna go on a date?” The words are as effortless as usual but he finds himself holding his breath for the reply.

But Cass just seems perplexed. His brows are furrowed and that blissed out expression has vanished.

“Why are you asking this?”

Spluttering, Dean tries to come up with a reply.

Of all the things he expected, Cass not saying yes wasn’t in the cards.


	22. Cass-a-Lisa

Dean groans. Why does Cass have to be so difficult? For a guy who supposedly wants to go on a date with him, Cass is incredibly uptight about the entire process.. Or maybe it’s the first time someone has asked him to go on a date. That has to be it - no one in their right mind refuses a date with Dean Winchester, except  _ maybe _ a newbie.

“Well Cass…” Dean says, reaching out to clap his shoulder. “Because we’re two consenting adults. Because freewill exists. Because you clearly crave intimacy and I can give that to you.”

Cass’ frown grows even deeper. “So you’re saying that you’re only offering to date me because you think it will help me?”

“Um… no. Cass, no.” It’s because I want to prove to myself that there’s nothing between us. However, Dean keeps that to himself. He has a feeling it won’t go over well with the angel.

“Then why?” Cass sounds genuinely curious. “To some extent, I understand why you let me have sex with you.”

Out of pure instinct, Dean glances at the door, just in case Sam spontaneously materialised in time to hear Cass’ declaration. For his actions he receives a droll look from the angel before he continues, “You have sexual relations with lots of people. The number of people you try to connect with emotionally is far less.”

“Way to make me sound like a floozy.” Dean says, only a little sour.

“You can’t deny your promiscuity Dean.” Cass rebutts, “I’m not judging you. I’m very thankful for it. Otherwise, I don’t think you would have been as open to helping me reach climax.”

“Now I sound like a whore.” Dean says it with a big grin, so Cass knows he’s just teasing.

“There’s no transaction occurring here.” He says anyway. “Unless you’d like a dollar from my wallet.”

With a playful shove, Dean shakes his head. “You’re a piece of work man.”

“Yes Dean, I remind myself of the Mona Lisa sometimes, too.”

To which Dean barks out a laugh. He tries to imagine Cass, in all his trench-coated angel of the Lord glory, trying to stay still long enough to be painted. That sends him into another fit of hushed laughter.

When the amusement fades, he realises that he  _ still _ doesn’t have an answer to his question.

“Why don’t you want to go out with me?”

Cass glances away, probably thinking of another way to stall Dean. But he isn’t about to be caught a second time.

“Just tell me.” Dean says, drawing Cass’ gaze. “Whatever it is… I’m a big boy. I can take it.”

“I told you my feelings… and suddenly you want to date me.” The angel exhales heavily. “You want to help me. Which, of course, is noble, but not romantic. If I ever date you Dean, I don’t know if I could survive the aftermath - especially since I know it isn’t real.”

He looks so sad about it that Dean immediately feels bad about it. Gently, he squeezes the angel’s shoulder and leans in just a little closer. Now that he gets where he’s coming from, Dean can put himself in his friend’s shoes. Being in love with someone, and fake dating them - knowing that everything is staged and will lead nowhere in the long run - doesn’t seem fun or romantic. It’s not fair that he does that to Cass, not if he  _ knows _ it will hurt him and tear him apart from the inside.

“I get it.” He assures, giving Cass what he hopes is a comforting smile. “No hard feelings man.”

Worry grips him by the balls as Cass just stares at him. Did he say the wrong thing? It didn’t seem like it, but then again, Dean is terrible at these things. Mentally, he takes stock of what he just said. Maybe it came off as dismissive or -

“But if you did have feelings…” Cass swallows tightly as he lets that thought trail off.

Now it’s Dean’s turn to be silent.

“I-I don’t know. And I don’t want to lead you on.”

“I know.”

This entire discussion is draining Cass. Dean can tell from the way his eyes dull and his shoulders drop. This entire endeavour was supposed to  _ help _ Cass, not make him feel even more shitty. But this isn’t something you fix. Lying would only hurt Cass more and so would the truth at this point.

“What if we tried it just once.”

“Just once?” Cass parrots, as though he’s trying to figure out what that means.

“Like a trial date.” It’s only as he says it does he realise how ridiculous he sounds. A trial date. Cass isn’t Netflix. Dean can’t take a free trial and ditch him after that.

But Cass answers before he has the chance to take it back.

“Okay.” And it sounds so hopeful it almost hurts.

No way can he take it back now.

Not that he wants to.

“It’s a date then.”

...

Strangely enough, when he leaves Cass’ room, Dean feels like he’s doing the walk of shame. Which is ironic, since he’s helping Cass overcome something and he should feel proud and not ashamed. Maybe it’s because they’re hiding it from Sam. 

There have been more than a few close calls, and instances where Cass just outright  _ told _ him, but Sam has managed to remain completely oblivious.

But when he enters the kitchen to find Sam lounging near the pile of half-ripe tomatoes, Dean turns just as red as he thinks about how close Sam was to discovering their secret. He hates lying to Sam, but he knows it isn’t forever… just until Cass figures his stuff out.

Dean grins to himself as he imagines Cass as Mona Lisa. With his hair grown out, wearing a dress and with the most constipated expression on his face.

**Notes for the Chapter:**

> So it seems that Cass is good at deflecting too... wonder where he learnt *that* (looks at the Winchesters)
> 
> Next up will be the actual date! (I dunno about you, but I think Dean is the type of guy to put out on the first date ;))


	23. The Sam Winchester Experience: Wine and Dine Em’

As Dean sits alone in his room, a terrible thought confronts him. 

He’s never been on a date. Not a proper one anyway, where he wines and dines the chick and then kisses her cheek goodnight. The large majority of his dates end with sex and him never seeing them again. Now, while his date with Cass will undoubtedly end in  _ some _ form of release, Dean will definitely be seeing him again the next day… and the next day and hopefully for all the other days after that.

The entire point of this is to mimic a real date - romance and all, so that Cass can say he had the experience. And so that Dean can figure out if what he feels extends beyond friendship.

Thinking of things to do is so hard. When he thinks of him and Cass having a night out, all that comes to mind are burgers and beers. And while that combo has been faithful to him for years… he just thinks that this time should be different - special - somehow.

He still has a couple hours to think… and so far, thinking of beer and burgers has made him ravenous. Making his way to the kitchen, he immediately pulls out of the burgers from the fridge.

“It’s ten in the morning Dean!” Sam’s harried voice jolts him.

“So?”

“Just-” Sam shakes his head, clearly giving up. Damn good move too, because once Dean has his mind set on something, there’s no going back.

As he oils the pan and lights the stove he belatedly wonders how Sam woos his dates. He’s always been much better at romance than Dean. It’s almost like it comes naturally to him. 

“Hey Sam?” Dean struggles to keep his voice even.

“Hmm?”

“Wh-when you go out on dates…” Dean trails off and stares blankly at the sizzling burger. This is stupid. He isn’t desperate enough to go to his  _ little _ brother for dating advice. But he catches a glimpse of the time on his watch and a familiar panic takes hold. Cass would be so disappointed if Dean messed this up for him.

So Dean sucks up his pride and ploughs forth. “Is it - do you -”

“Hold up.” Sam interrupt. “Is this you trying to be a dick and poke fun at me?”

“No!” Dean says, indignant.

Sam’s brows pull down as he frowns consideringly. “Then what is it then? It’s not like you to - you know.”

Dean swallows tightly and turns back to his pan. The smell of the meat is becoming stronger now, signaling that the burgers are almost done. “I like someone.” Dean says finally. “Well, I think I do. We want to go on a date - like a trial, sort of - to see if we’re compatible. And all I can think of is burgers and beer.”

When he turns to face Sam again his brother’s eyes are wide - almost comically so.

“You’re serious.” Sam breathes after a beat.

Dean nods once.

“Who is it?” Sam wonders as he tucks his hair behind his ears. 

Now there’s the kicker. Sam looks almost proud of him now, but if he knew that he was doing this for Cass - and about all the  _ other _ things he’s doing for Cass - that pleased grin would likely be replaced by a look of scorn. 

“I don’t wanna say.” he says instead, knowing that Sam won’t give up without some sort of answer. “It’s still early and I don’t even know how I feel.”

“You’re here.” Sam says with a grin. “Asking  _ me _ for advice while your burgers are turning to coal.”

Dean yelps and whorls to flick off the burner. This thing distracted him so much that he completely forgot the burgers.

“Which tells me that you  _ do _ feel something.”

Dean scoffs

“If you didn’t care, you wouldn’t bother.” Sam returns, seeming pleased with his deduction. “I know you, Dean.”

Remaining silent, Dean glares at him petulantly.

“So anyway. How do you do it? Wine and dine em? Tell me about the Sam Winchester experience.”

With amusement, Sam shakes his head. “It isn’t rocket science Dean. Just do something you both like. Beer and burgers isn’t a half bad idea. You could do dinner at a nice restaurant. Or go bowling - or maybe not. You’re too competitive.”

Dean bristles at that, but doesn’t deny it.

“It doesn’t have to be expensive or anything. Just something fun for the two of you.”

“Well that was useless.” Dean snips. “You haven’t told me anything I don’t already know.”

“Well it always depends on the person.” Sam says, slightly exasperated. “Maybe if you told me a little more about -”

Dean shakes his head. “No. I already told you more than I wanted to. Stop fishing.”

With a grin, Dean cocks his head. “I didn’t need you anyway.” He says, before walking out of the room.

“Fishing.” he mutters to himself. Cass will like that. It’s quiet and peaceful. It’ll give them time to talk and eat and hangout. Dean mentally pats himself on his shoulder.

It’s only when he hops onto his bed does he notice the distinct  _ absence _ of a burger. He groans. Sam is probably just waiting for him to come back for it like the little bitch he is.

But Dean isn’t one to let a burger go to waste, so he makes his way back to the kitchen, already cataloging all the things he needs to make this date perfect.

Rods, bait, a blanket, some food and drinks.

Satisfied, Dean nods to himself, already envisioning how perfect their evening is going to be.

Dean Winchester can wine em’ and dine em’ after all.

**Notes for the Chapter:**

> I know I promised the date in this one but I got carried away with the Sam and Dean interaction


	24. You Look Great, Man - Dean Winchester™

When Dean sees Cass decked off in his suit and trench coat combo he winces. He certainly doesn’t mean to. But he tries imagining him wearing that in the water. At some point Dean hopes that they’ll get to swim, or if they’re bold enough in the moment, skinny dip.

He simply doesn’t have the words to express that right now. Because Cass looks  _ great.  _ If he was a chick, he’d be drooling all over the guy. Everything is neatly pressed and even his tie is on straight and his hair brushed back. 

Because he’s observant like that, Cass notices his shifty expression immediately and frowns. “What’s wrong?”

“Nothing.” Dean says in a rush. Obviously, Cass spent time on this get up. Asking him to take it off - and not in the sexy way - would be rude, and not the way Dean wants to start off their date.

“You don’t like my attire.” Cass looks crestfallen and Dean rushes to fix things.

“No. No. You look great, man.”

With a furrowed brow, Cass adjusts his tie. “Wikipedia says that this is what one wears on a formal date.”

Dear God… Wikipedia. This dude needs him more than ever if he’s getting dating advice from friggin’ Wikipedia.

“Maybe… if we were goin’ to a restaurant or somethin’ fancy.” Dean muses. “But I was thinking we’d get our toes wet. Do some fishing!” He says excitedly, hoping to get Cass on board with the idea.

Instead the angel seems confounded. “But - this is a date, right?”

“Yes.” Dean assures. “Definitely a date.”

…

The drive over to the little stream, is unnaturally quiet. Cass looks so stiff that Dean just can’t seem to get any words out. He’s nervous too. About the date. About what it could mean if things go well. But given Cass’ stony expression he doesn’t have to worry about things going well. He finds himself wondering what he did wrong… how he managed to screw this up before they even started.

Dean shakes his head in despair. He  _ always _ does this. He always ruins things. Half of him wants to put them both out of their misery and head back to the bunker, but another part of him, wants to give it his best shot. That part wins and Dean just readjusts his grip on the wheel and stares grimly at the open road.

“Cass?” It takes him five miles to muster up the courage to utter even that single syllable.

The moment his pet name rolls off his tongue, Dean regrets it. He doesn’t know what to say next so he just sits there dumbly, attention torn between the empty road and Cass’ pointed stare.

It takes another mile before Cass replies, his voice gruff and low. “D- Do you still want to do this?”

“Yes.” Dean says vehemently. His eyes dart to Cass’ “Do you?”

The angel gives him one crisp nod… which does nothing at all to reassure him.

Dean pulls over. No way is he having this conversation with Cass’ side profile while having to glance at the road to see if they’re about to hit anything.

“Man.” He breathes, turning to face Cass fully. “I’m tryin’ here Cass but I don’t know what went wrong. What did I do?”

With a hefty sigh, Cass turns to face him too. His eyes look sad. This wasn’t how they were supposed to start off their date.

“I read on the internet that courting usually involves dinner at a nice restaurant.”

Oh. That’s why Cass put all that effort into looking good. Dean feels like a dick. He wanted this to be a fun surprise for Cass but he ended up ruining the outlook his friend had for the night.

“Well sometimes.” Dean replies, unsure of what to do.

“But I understand why you’re doing this.”

If there’s one thing Dean knows… it’s bitterness. And Cass’ voice is laced with it.

“Why do you think I’m taking us fishing?” He prods carefully.

Cass scoffs at him and turns to look out the window. “You’re you, Dean. You don’t want to be seen publicly on a date with a - male.”

“You couldn’t be more wrong.” Dean protests, resting a hand on Cass’ shoulder.

The angel turns to look at him, he wears his doubt clearly on his face.

“I uh, I talked to Sam.” Dean says in a rush.

Cass quirks a brow, confused.

“He’s usually the one who’s good with stuff like this. I was gonna take you for beer and burgers Cass.” Dean says, looking into Cass’ eyes to let him know that he’s sincere. “But I didn’t think that was good enough. I wanted it to be fun… and romance-y and everything you ever wanted it to be and I’m so sorry I screwed that up.”

“You talked to Sam?” Cass parrots, staring at him wide eyed.

Dean flushes. “I didn’t tell him it was you. But yea, I was spitballing ideas with him. If you want I’ll take up to the nicest place in town. I swear I’m not embarrassed or anything. Just say the word and we can go.”

“I just thought you didn’t want to be seen with me.” Cass admits, looking sheepish. “I should have known better than to jump to conclusions like that. But I admit, this all has me feeling a bit off balanced.”

“Amen.” Dean mutters, thinking about how stressed he’s been.

“But I do love spending time with you Dean.” Cass continues, his features soft and open. “Over the eons, nothing has brought me more pleasure than your company.”

Dean ducks his head at the unexpected compliment. “Wow, uh Cass -”

With a small smile, Cass leans in, pecking Dean on the lips. It’s chaste and nothing like they usually do. But for some reason, it lights Dean on fire. It’s so intimate… so special he can hardly think straight.

“You need to learn to accept a compliment gracefully, Dean.” Cass play chastises.

Dean just sputters wordlessly causing Cass to throw him an amused look.

It doesn’t take long before his friend has mercy on him. “Now that we’re both on the same page, I really can’t wait to go fishing with you. I know it will be fun. With you, everything always is.”


	25. The Bromance of a Lifetime

**Notes for the Chapter:**

> I'm sorry this took so long.... But leme tell ya, I feel Cass, being in love with someone who doesn't know is hard as hell. Wrote this with like a bottle a Jack and some vokda but I think it's fine.

By the time they pull up to the little creek, they’re in much higher spirits than they were at the start of their date. Dean makes Cass wait in the front seat while he walks around to open the door for him with a shit-faced grin. Cass graciously steps out and almost blushes at the action, which makes Dean’s stomach flip, because he’s done something good at last.

Dean decides that they’ll enjoy the picnic first and then fish.

“How come?” Cass wonders when he suggests it.

“Well,” Dean states, “I figure the fish ain’t leaving… but who knows what kind of animal is out there waiting to ‘steal our pic-i-nic basket.’”

With a playful chuckle, Cass shoves at his shoulder, “There are no talking bears here, Dean.”

“What?” He can’t help but tease. “Did you check?”

Cass gives him a bashful smile. “Maybe if this goes well we can make that our second date.”

Dean grins. “Hell yeah, man.” He scoffs. “We’ll hunt Yogi Bear and Boo Boo.”

“Is that pie?” Cass wonders, peering past Dean and into the basket.

“Course.” Dean says. Like he wouldn’t bring along some pie. Ha.

“Let’s have some.” Cass says, perking up.

If this was anyone else they’d be on  _ Dean _ for trying to have ‘dessert’ before the actual food. He must look surprised because Cass just chuckles, “I know you must have wanted to eat this since you packed the basket.”

Dean’s lips twitch at just how true that statement is. “Damn straight, Cass.”

Which only causes Cass to snort loudly.

Brow raised, Dean gives him a confused look.

“That’s the only thing straight about this.” He says wryly, causing Dean to choke out a laugh.

Even he can’t argue with how accurate that statement is.

Between the two of them, the pie is devoured in under an hour while they lay on the blankets.

“Oh, man.” Dean yawns. “I think I’m too stuffed for any of the other stuff.”

Cass gives him an amused look. “We both know that the contents of that basket won’t survive the evening.”

And… Cass was right, their little feast didn’t last. Dean scarfed down the potato salad, the only salad he’d ever eat since the lettuce is basically mayonnaise. Meanwhile Cass makes quick work of the PB&J sandwiches and then the small bottle of honey. The angel literally tilted his head back and poured the entire thing down his throat, leaving Dean to stare at him in stunned silence.

“No gag reflex.” Cass reminds him.

Which, yeah, is totally unnecessary because Dean will never not remember  _ that _ . Especially given what it’s been doing to his dick recently. There have been multiple times where Cass swallowed him down and he came embarrassingly fast. Of course Cass was always a good sport about it. In fact, he almost seemed excited by the prospect of making Dean blow his load in two seconds flat. But that really isn’t. Now that he knows Cass’... feelings. He can rationalise certain things better. 

He suspects that Cass likes making him come so quickly because it’s a sign that Dean’s body reacts positively to him. It’s not exactly a strange kink either, because Dean himself enjoys it more when he knows his partners are feeling good too. And there’s something special about seeing someone you have feelings for… come apart under your hands. So he gets the appeal, he really does. But he  _ does  _ wish that Cass wouldn’t grin at him like he won the lottery after, while Dean is still sheepish about being a two second wonder.

“Dean.” Cass calls, getting his attention.

“Yeah.” He pries his stuffed ass off the cloth and moves over to see what Cass is looking at.

Dirt?

“Um…”

“Shh!” Cass commands and Dean’s mouth snaps shut as he waits for… whatever is about to happen.

This has the distinct feeling of a prank. But Cass doesn’t  _ do _ pranks, so…

Just then a tiny worm sticks his head out of the dirt and Cass latches onto it immediately, drawing it’s stringy, worm body out of the ground even as the poor thing tries to curl in on itself.

With a cringe, Dean shifts back as Cass almost shoves the thing into his face.

“Man!” He barks, shooting back some more.

Cass just does his trademark head tilt, still holding the worm of course.

“I found the bait, Dean.”

The thing wiggles, trying to wrest out of Cass’ two fingered grip. Dean feels his  _ very _ full stomach churn. “Aw man, that’s horrible.”

He turns away, pressing a hand over his mouth and swallowing tightly.

“Aren’t worms bait?” Cass wonders from behind him.

“Yes.” Dean says slowly. “But - I don’t like  _ seeing  _ them… you know…  _ alive. _ ”

How’s he supposed to get a wriggling worm onto a hook. If it’s dead, that’s fine.

When Cass rests a hand on his shoulder, Dean double checks that he’s worm free, which he thankfully is. Although, he does look a little smug. “You’re squeamish.” He almost sounds happy about that.

Dean just scoffs.

“You know… there are lots of worms like this in Sam and I’s garden.”

“Which is exactly why I stay at least a mile away from that thing.”

Cass chuckles.

“Let’s fish then. I assume you brought bait that  _ won’t _ make you want to vomit.”

…

Dean doesn’t do much fishing. He spends most of his time positioning Cass right and stopping him from yanking the rod up at the slightest shift in the air. The first time he thought he felt a tug, he whipped the like up so fast and violently, it almost took out Dean’s eye.

Eventually, with much coaching from Dean, Cass was able to get a bite. The happiness that spread across his face made up for not getting a bite himself. Just hanging out with Cass, positioning him on the dock, keeping his hands steady on the rod and eventually, slowly reeling in his bite somehow seemed just as fun and relaxing as if he were fishing himself.

But as they pack up their gear, Dean realises how different this was to a real date. He isn’t the only one doing the heavy lifting. He isn’t thinking about getting into Cass’ pants. He didn’t have to mince his words or dance around how he really felt… which can be attributed to the fact they’ve known each other for years. But it doesn't circumvent the fact that this felt  _ nothing _ like a date.

It felt  _ better. _

Because they were just hanging out… him and Cass. There was no pressure, no fear. Just them.

It didn’t feel like a date… because it was a date. It wasn’t romantic. They just hung out. It was  _ normal. _

“So, when will be back to hunt Yogi?”

Cass’ voice almost makes Dean crumble. But he promised himself that he’d give this a shot. And he had. He won’t lie to Cass about this. Not when the angel had made a point about being honest about his reservations from the start.

“We shouldn’t.” Dean mumbles, unable to bring himself to even look at Cass. “This didn’t feel like a date to me. It- it felt like the two of us were just hanging out. Like any other day.”

“Dean.” It’s only then that he forces himself to look at his friend. Cass is pissed… livid. His expression doesn’t offer much comfort either.

“Cass-”

The angel cuts him off swiftly once more. There are words right on the edge of his tongue whatever it is, it’s important enough for Cass to need to compose himself to say it. “Dean I-” and then he stops.

It’s abrupt and even after a minute, Cass doesn’t make a move to continue.

“What?” Dean makes sure to keep his voice soft. He doesn’t want to be angry right now. They just had a fun evening and he doesn’t want to ruin it.

“Nothing.” Cass whispers.

“Come on.” Dean prods. “It clearly ain’t nothing.”

The fire returns to Cass’ eyes. “Tell me, then, Dean, which other  _ friend _ of yours would you do this with?”


	26. Bye Panic

**Notes for the Chapter:**

> Hehe I stole a little dialogue from the show

The first thing Dean tries to remember is which of his friends aren’t dead.

The second, is how to answer Cass’ question.

He wouldn’t do this with Jody or Donna or Garth or -

But none of them  _ get  _ him the way Cass does. Because Cass is his best friend. Nothing more than his best friend.

Right?

They tried this thing out to see if things could work and Dean thinks they can’t because their ‘date’ went normally. It felt like almost any other chill session with Cass. So that means they’re incapable of being together like that - right?

When Dean realises he can’t properly answer that question, the panic renders him mute.

And Cass is just staring at him.

Waiting for a reply.

He  _ deserves _ a reply.

And Dean wants to give him one. He just can’t find the words to express anything at all.

“What friend would you make love to and even attempt to take on dates, Dean?” The angel demands. “I am genuinely curious. Dean you know-” and he continues talking even though Dean can’t understand a single word coming out of his mouth.

Dean wants to demand that he shut the hell up and be happy he even tried this dating thing. But he knows how much that would hurt Cass. Sometimes Dean forgets that Cass is in love with him. Because he doesn’t act any different than he did before the big reveal… but then Cass has been in love with him for  _ years. _ Maybe he’s always acted like it… Cass isn’t the type to hide his feelings; much less even understand the need to even bother hiding them.

Yes, Cass deserves answers. But Dean also deserves one friggin moment to process what the hell just happened. Because what Cass is implying… Dean isn’t ready to face yet.

Which is strange since he was the one to suggest this date in the first place… to sort out their feelings. Yet it seems that whatever those feelings are just became more jumbled.

“Car sex.” Dean’s brain supplies, stunning Cass into silence.

They both stand there, marinating in Dean’s lack of filter.

He doesn’t even know where that idea came from. All he wanted was for Cass to  _ stop _ talking about how everything he’s done makes no sense.  _ Get in line buddy, I can’t even make sense of what’s been going on recently, _ Dean thinks bitterly.

“Dean I am being serious. I think I deserve-”

Holding up a hand, Dean silences him. “I know. I know you deserve someone who is together - who can express their feelings like a normal person.” He deserves so many things Dean won’t be able to give him and despite knowing that, Cass doesn’t seem to care.

The angel’s expression goes sad.

“But Cass this is hard for me.” Dean admits, looking off to the side. “I was wrong to - to dismiss our date so quickly, but the things you’re saying… the things you’re implying… I can’t face it. Not now. You know?” He glances at Cass, terrified to find pity in his eyes, but relieved to find understanding instead. “My whole life… I thought of myself this - this way and now -”

“Dean.” Cass engulfs him in a hug that almost knocks him off balance. “You mean everything to me. I know - I know how you see yourself. I know that pushing you like that wasn’t fair. Especially given all that you’ve done for me. I was just… peeved that you didn’t see our evening the way I did.”

“I - It was awesome Cass.” Dean assures, breathing out a sigh onto Cass’ shoulder. “I never meant to take away from that.”  _ I’m just scared.  _ He doesn’t voice the last part but Cass tightens his grip.

“Do you know what I think?” The angel asks lowly, his breath ghosting past Dean’s ear.

He shakes his head against Cass’ shoulder. It feels like Cass is tethering him right now - that if he lets go Dean will just float away.

“I love you…” Dean’s heart races at the words. The words are whispered, said softly but Cass’ voice is proud. Just hearing those words again soothes something inside him. But the angel isn’t done yet, “And I think… that I should tell you that more. You never need to say it back, but I know you care for me, maybe not in the way I crave, but you do. And I think, that you deserve to know that you’re loved. Not because I want you to say it back. But because it’s a truth you need to hear more often.”

Dean is left utterly speechless.

Then, Cass pulls out of the embrace, still keeping his hands on Dean’s shoulders and gives him a long, searching look.

“I love you, with everything I have.”

And Dean wants to say something equally profound… something that causes Cass to feel the same butterflies in his stomach as Dean does. Instead, he stands there, mouth gaping like a fish.

The thing is, Cass doesn’t even seem to mind his lack of response. He just stands there with a proud smile on his face, gazing at Dean with unmistakable love in his eyes. It’s that expression that leads Dean to believe him. That he simply  _ wants  _ to say it. To express himself. 

Cass’ expression is so open and free. So light. Dean is almost jealous.

“I don’t know what to say.” He breathes, lowering his eyes.

“I do.” Cass replies instantly, reaching up to tilt Dean’s chin to the side - to where they parked Baby. 

When Cass smiles, there’s nothing tender about it. His expression is ravenous. Lips trailing up to Dean’s ear, he nips it not so gently, promoting a full body shiver from Dean before whispering in the most seductive voice Dean’s ever heard: “Car sex.”

**Notes for the Chapter:**

> so I guess the next chapter is gonna contain some raunchy car sex ;)
> 
> Some spoilers for 15x15-20 are down below so ignore if you don't wanna see it.
> 
> Honestly this whole mess is sending me. After Castiel's confession in 15x18 I considered saying some stuff to someone because his whole 'happiness is in the being. in just saying it' really got to me. And I was really considering doing it. Then, they erased the confession and it's impact so completely from the show.


	27. Eyes Like the Sky

**Notes for the Chapter:**

> I'm sorry. I'm not dead. Just having a rough go

Cass almost bundles Dean over in his haste to get to Baby. But when Dean’s back finally hits Baby’s sleek exterior, Cass freezes. The angel looks at Dean head on, staring soulfully into his eyes. Even more intently than usual, which is sayin’ something. And Dean is left standing in awe of his expression. The attentiveness on his face and the love swirling in his sky blue eyes.

“Oh, Dean.” he whispers, low and sultry, his voice dropping to an absurdly guttural drawl. “The things I’ve dreamed of doing to you.”

Dean wants to point out that angels don’t sleep. So they shouldn’t be able to dream… but Cass presses their lips together and a storm surges inside Dean, washing away any traces of his silly musings. Cass’ hips are grinding against his at a tempo that has Dean bucking into it and groaning against Cass’ plush lips. His dick is hard, pressing against the seam of his pants, and he’s more thankful than ever he decided to wear boxers today, else his sensitive head would be up and close with the zipper.

Against him, Cass is equally hard and Dean can practically sense the desperation coming off of him. The guy hadn’t had an orgasm for millions of years, figures he’d be super horny.

Forsaking his lips, Cass nips and sucks at his neck attentively, leading Dean to lean bonelessly against Baby’s slightly warmed metal frame.

Hands slipping under Dean’s shirt, Cass strokes across his stomach languidly. It makes Dean a little self conscious and he falls out of the trance. That’s when he realises: “Hey lemme touch you too.”

He moves to shift his hands from where they were tightly wrapped around Cass but the angel shakes his head. “Not yet. I’m going to try something.”

The way he says it has Dean’s breath stuttering out in a broken, “O-okay.”

Slowly, his fingers snake into the wasit band of Dean’s pants, flicking open the button and running over his hard cock. A harsh exhale is punched out of him as Cass finally gives him a proper stroke. And then Cass drops to his knees, shifting Dean’s pants down to his hips and looking up at him searchingly.

And Dean is too lost in his eyes for words, so he just nods his consent which makes Cass smile. Damn, the way he looks… on his knees in front of Dean’s hard cock, looking up at his with those eyes. Those damn blue eyes.

Warm, velvety softness makes it’s way down Dean’s cock as Cass swallows his length slowly. Looking up at Dean the entire time. Dean. Whose mouth is hanging open as he struggles not to blow his load.

When Cass’ tongue slips out to nudge his balls, Dean jerks, his cock hitting against the back of Cass’ throat. The angel doesn’t even flinch, he just hums around Dean.

And then Cass proceeds to blow him. It’s hard and fast and dirty and Dean can only hear himself moaning wontonyly, with his head thrown back as his hard, sensitive dick is teased to it’s limits by Cass’ mouth.

Cass licks and sucks at him until he’s right at the edge, one hand flying down to keep his head in place. Only, he pulls off, leaving Dean’s dick twitching futilely, desperate for an orgasm.

Standing, Cass looks rather pleased with himself, going so far as to smirk and trace a finger around Dean’s head.

“Car sex.” He reminds gently. “We haven’t made it inside the car yet.”

Oh man. Dean is in for one wild ride.

…

Dean does a double take.

Cass is on his back, legs spread. Both of them are gloriously naked. Only… there’s blue where there shouldn’t be blue.

Running a hand over Cass’ balls, Dean gently touches the sparkly gem over Cass’ hole.

“You’re wearing a butt plug?” Dean’s voice is almost a whisp.

And even though he’d been the one with all the bravado this evening, Cass suddenly looks bashful.

He gives a mute not, his legs tensing.

“Man, I-” Dean breaks off with a swallow. His eyes darting between Cass’ eyes which are even bluer than the jewel on the plug.

“I was hoping…” Cass let’s it trail off.

Dean is stunned.

“We don’t have to do this.” Cass says quickly, scrambling into a sitting position. “I know you didn’t actually mean it when you said it.”

Dean shakes his head. “No. I wanna.”

He gets a disbelieving frown.

His hand moves to Cass’ knee. His very naked knee, and Dean once more marvels at how comfortable they are with each others’ nakedness. “I… just thought that, you -”

“That I?”

“Would want to be on top.” Dean mumbles.

“Oh.” Cass whispers, as though he’s just had a revelation. “Dean, I don’t care if I’m on top or the bottom. Just being with you. It’s everything I could ever want. And I want this. I like the way this toy feels inside me… and I could tell you liked it too.”

Dean flushes. “I was surprised… but yeah. It’s - it’s hot.”

“Do you still want to do this?”

Of course he does. And Cass is right in front of him, wearing a  _ plug _ and Dean feels overwhelmed. Now that he doesn’t have to worry about who’s ‘on top.’ He can worry about the other aspects of gay sex.

Like anal.

Like stretching… and lube. Because healing angel grace or not, Dean ain’t going in dry. If he’s doing this, he wants them  _ both _ to feel as good as possible.

“Did you bring lube?”

“Of course Dean.”

“And protection?” Dean asks teasingly, hoping to lighten the mood between them.

“Of course, Dean.” He repeats. “My angel blade is right in my coat.”

“And your coat is where exactly?” Dean wonders as he playfully turns the plug.

The gasp he elicits has him doing it again.

“Wherever you flung it Dean”

Slowly he draws the plug out slightly, watching Cass’ reaction carefully. He seems to be enjoying it. No signs of pain or discomfort…

Dean presses the plug back in, watching as the skin around Cass’ hole seems to suck it in greedily. “Ready, Cass, I’m going to open you up?”

His fingers remain on the plug, moving it in and out carefully, his eyes entranced by the gleam of blue that reminds him so much of Cass’ eyes. But when he looks up, he realises that the plug could never hold a candle to Cass’ eyes. The blue in them is richer, yet lighter and so vivid. They make Dean want to give him the world, because when he sees those eyes, he sees himself falling through the sky - falling deeper into Cass - and loving every second of it.


	28. Car Sex

For who knows how long, Dean is thoroughly entranced by the gleam of Cass’ butt plug. As though in a trance, he keeps moving it in and out, turning and twisting it and wrenching the most seductive noises from Cass. One hand lightly strokes the inside of the angel’s thighs in time with the movements of the plug.

A particularly high whine has his eyes drifting up. Cass’ expression is positively wrecked. He’s flushed and flustered and so very aroused.

“Dean!” Cass moans, lifting his head to peer down at Dean as he works the plug. “Dean, if you don’t ‘fuck me’ right now I’ll die.”

Dean bursts into a fit of laughter which causes Cass to glare stonily at him. “Man did you just -” He breaks off to take a necessary breath. “Air quotes? Really?”

“Dean.” Cass warns in a tone that halts Dean’s laughter.

In reality, the reason he’s been going at this glacial pace is because he has no clue what to do. He knows he needs to stretch Cass with his fingers. But the thought of putting them  _ there _ is a little weird. He liked it when Cass did it to him. Cass liked it too. A lot.

But somehow this feels different.

Suddenly, Cass’ arms are around his neck, dragging him down and kissing away all his doubts.

Cass is enjoying this. Cass wants this.

Hell, Dean is now far gone enough to admit that  _ he _ wants this too. His cock is hard against Cass’ stomach and his skin is tingling with sensitivity from how turned on he is. So he reaches down and slowly draws the plug out one last time before tossing it over to the front seat. 

“Where’s the lube Cass.” He whispers, pressing a kiss onto the angel’s nose.

The move leaves Cass in stunned silence, and the angel points mutely to his pants.

Dean reaches for it with a burst of speed that both surprises and embarrasses him. But when his fingers pop the cap, he feels anything but embarrassed. He feels excited. Raw. Passionate. There’s a guy spread out before him like a friggin’ buffet. His pleasure is all Dean’s to control. The feeling is heady. Watching Cass tremble as he slicks his finger with lube.

Having Cass like this means everything to him. The trust that the angel has placed in him means everything to him. Dean is determined make this perfect.

The first centimeter of his finger slides in easily, almost as though Cass’ hole sucked it in. Dean’s eyes flit between their connection and Cass’ face, not wanting to go too fast.

As he slips more of his finger inside, Dean makes a concerted effort to find and prod Cass’ prostate. It takes him a few tries and another finger... but the noise Cass makes when his finger hits it is so worth the stiffness in his wrist.

Clamping down on his fingers Cass moans wantonly, pressing himself further into the leather sheets.

“Dean. Please.”

The plea almost shatters Dean’s composure, but he holds fast. There’s still a bit of stretching to be done.

“One more finger Cass.” He assures, sliding the third one in.

For the first time since they started, Cass makes a noise of discomfort that stills Dean’s hand.

“Keep going.” Cass breathes. And Dean does, moving slowly until three of his fingers are buried deep inside him.

It’s not as weird as he thought it would be. The thought emboldens him as he stretches Cass, occasionally giving his cock a few strokes to keep him hard.

“Dean I’m ready.”

Drawing a steadying breath, Dean withdraws his fingers and slowly makes his way up Cass’ body to kiss him. It’s a breathless sort of kiss, but Dean needs the closeness now. And he thinks Cass does too.

“I’ll go slow.” He promises.

Cass nods, swallowing a little nervously. “I trust you.” He says. “I want this.”

“Me too.” Dean murmurs, reaching down to give himself a few strokes. It’s the first time he’s touched his cock since he started stretching Cass and he bites his lip at how good it feels. The way Cass wrapped around his fingers… that warm tightness around his cock would feel amazing.

Gaze never wavering, Cass stares at him as he generously coats himself with lube, spreading a little extra over Cass’ hole.

The feeling of Cass’ rim stretching over his head is heavenly. Dean groans his pleasure into Cass’ neck whilst the angel clamps his legs around his hips, not drawing him closer, but just holding him steady.

The next small push has Cass exhaling sharply, his fingers digging into Dean’s shoulders.

“Dean.” Cass all but moans. “More. You feel so good.”

“Ditto.” Dean grunts, feeling Cass clench around him. He’s barely half way inside and Dean is struggling to keep himself in check. “But, I’m really turned on. Not sure how long this is gonna last.”

Cass scoffs at him and gestures to his own hard cock that is steadily weeping onto his stomach. “I’ve been close since you started stretching me.”

Dean smirks then, purposefully lowering himself enough that his cock drags over Dean’s stomach.

Tensing, Cass mewls at the contact. But then he glares at Dean for teasing him and tenses his muscles around Dean, punching a debased moan from his lips.

Looking beyond pleased with himself, Cass shifts his hands to Dean’s hips, drawing the rest of his cock inside himself.

When he finally bottoms out, Dean can hardly see straight. Everything is super sensitive. He can feel Cass wrapped around his erection. He can feel their hard nipples rubbing together. The warm thighs locked around his hips. Most importantly, he can see the expression on Cass’ face; the love and lust and overwhelming emotion that Dean feels echoed within himself.

He’s had sex many many times.

However, he’s never felt as close to someone as he does in this moment.

They both lie there, pressed together for a long moment. Simply enjoying how close they are.

“You okay?” Dean wonders softly, noting that Cass hasn’t spoken for some time.

His friend nods mutely, biting his lips. “I always wondered…” He lets the thought trail off breathlessly. “I always wondered what this would be like. With you.”

The rawness of Cass’ voice stunns Dean.

“Is it just like you imagined?” Dean certainly hopes it is. He’s never felt anything like this before.

“Better.” Cass admits, sighing softly. “So much better, Dean.”

“I know.”

And then Dean starts moving. First with slow, shallow thrusts. Then he progresses to faster, longer strokes that make Cass tremble beneath him and cant his hips up, chasing after the stimulation.

It feels like all the time in the world has passed and at the same time, like time is standing still for them.

Dean’s mind blanks, except for the harsh exhales that fill the Impala and the slick sounds of their bodies moving together and the steady presence of Cass undulating beneath him.

“Dean. Dean.” he chants, drawing Dean further into bliss.

“Cass.” He replies, unable to find the words to express just what he feels in this moment. Though, he figures ‘Cass’ is accurate enough, if only because every feeling he has is linked to the man beneath him.

All too soon, Dean feels his balls tighten. His rhythm falter… 

“Are you close?” he manages.

Cass nods desperately, one hand leaving it’s place on Dean’s hips to stroke himself. But, in a daring move, Dean bats it away.

“No.” He says, reaching down to do it himself. “I’m taking care of you Cass. Just enjoy it.”

In no time at all, Cass’ breaths turn into moans and then a series of sharp cries as he comes. His body is writhing as Dean fucks and strokes him through it and his lips are parted as the most delicious of sounds fall from his lips. Dean strokes him until he whines from the sensitivity and only then does he allow the angel to catch his breath.

With glassy eyes, Cass stares up at him, giving him a sated smile. “Dean…”

Dean feels himself twitch at the loving tone.

Cass clearly notices too because he says it again. “Dean… are you close?”

“So close.” He whimpers, shifting his hips slightly.

Cass’ hands run down his back before gripping his ass tightly. “Let go Dean.”

And he does. A few hard thrusts and his vision goes white as the most powerful orgasm of his life rolls through him. His toes curl, his hips stutter, his breath stalls. With one strangled cry he’s coming hard.

When he comes back to himself, he finds Cass staring at him, entranced.

“You’re beautiful.” He whispers, running a thumb across Dean’s cheek.

**Notes for the Chapter:**

> I'm so sorry I haven't updated anything in so long. Life has been tumultuous.
> 
> *this is pretty heavy so viewer discretion is advised*
> 
> Eventually, I decided to mention that my feelings were something more to the guy. He agreed to try things. All was well for about two weeks. Then he mentioned not feeling well but then he said he get better. So I didn't think twice about it after that. But he hasn't messaged me or even been online in about a week - which is very strange for him. And it felt so very off to me. Even if he's not going to be online, he always gives me a heads up and it's something like a 'We Got Mail' situation. So we don't know the other person's real identity. So I'm ashamed to say I did some stalking. I know enough about him to find him - I didn't before because I didn't want to break his trust. I found an obituary that matches him almost to a T around the same time he stopped replying. 
> 
> I hope I'm just being paranoid. Or maybe it wasn't actually his. Maybe his phone broke or he's swamped with work. Or maybe he got bored. I don't know. And the uncertainty is kinda wearing away at me and making me think the worst and feel disconnected from everything.
> 
> So I'm in limbo. I hardly have motivation to do anything - even write. But rest assured, I will finish all my WIPs in due time.


End file.
